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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:27:12 UTC

Update Date

2022-03-07 02:53:49 UTC

HMDB ID

HMDB0033697

Secondary Accession Numbers

HMDB33697

Metabolite Identification

Common Name

Melilotocarpan C

Description

Melilotocarpan C belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, melilotocarpan C is considered to be a flavonoid. Melilotocarpan C has been detected, but not quantified in, herbs and spices and pulses. This could make melilotocarpan C a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Melilotocarpan C.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0033697
     RDKit          3D
Melilotocarpan C
 42 45  0  0  0  0  0  0  0  0999 V2000
   -6.8139   -0.3034   -1.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9018   -0.4364   -0.0546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5635   -0.0955   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9886    0.4273   -1.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6509    0.7363   -1.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8736    0.5466   -0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4494    0.0262    1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937   -0.2916    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3396   -0.8188    2.1956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6966   -0.1863    2.2089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909   -0.0464    2.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1437    1.0873    1.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5876    0.9040    0.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7658    1.3114    1.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101    0.9763    1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0640    0.1982   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2961   -0.1562   -0.6123 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4941    0.2495   -0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892   -0.2264   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9458   -1.0101   -1.8414 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9772   -2.4138   -1.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6617    0.1272   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3582   -0.1792   -0.6081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600    0.8969   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3191    0.6997   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3907   -0.3777   -2.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6301   -1.0684   -1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5948    0.5865   -2.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2263    1.1507   -2.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3162   -1.0789    2.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1413    0.0465    3.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084   -0.9846    1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0808    2.0803    1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7009    1.9139    2.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9310    1.3081    1.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3505   -0.1142   -0.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6442   -0.1790    0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6142    1.3363    0.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5462   -2.9704   -2.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -2.7122   -0.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094   -2.7700   -1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2291    1.8102   -0.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 24 12  1  0
 24  6  1  0
 22 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 24 42  1  0
M  END


  Mrv0541 05061307182D          

 24 27  0  0  0  0            999 V2000
    6.8689   -1.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842   -3.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -4.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -2.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -2.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980   -1.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156   -2.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5926   -0.4994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450   -2.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -3.6213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453   -0.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -2.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  4  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14 12  2  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 10  2  0  0  0  0
 16 14  1  0  0  0  0
 17  9  2  0  0  0  0
 18 13  2  0  0  0  0
 18 17  1  0  0  0  0
 19 14  1  0  0  0  0
 20  1  1  0  0  0  0
 20 12  1  0  0  0  0
 21  2  1  0  0  0  0
 21 13  1  0  0  0  0
 22  3  1  0  0  0  0
 22 18  1  0  0  0  0
 23  8  1  0  0  0  0
 23 16  1  0  0  0  0
 24 15  1  0  0  0  0
 24 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033697

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(OC)=C3OC)C1CO2

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c1-20-12-6-5-10-15-11(8-23-16(10)14(12)19)9-4-7-13(21-2)18(22-3)17(9)24-15/h4-7,11,15,19H,8H2,1-3H3

> <INCHI_KEY>
ITMVICNONDPRSU-UHFFFAOYSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.3319

> <EXACT_MASS>
330.110338308

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.9244648262663

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,14,15-trimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-6-ol

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
2.1938808649999997

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.187222117872176

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2355737862336875

> <JCHEM_POLAR_SURFACE_AREA>
66.38000000000001

> <JCHEM_REFRACTIVITY>
85.9875

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
melilotocarpan C

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033697
     RDKit          3D
Melilotocarpan C
 42 45  0  0  0  0  0  0  0  0999 V2000
   -6.8139   -0.3034   -1.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9018   -0.4364   -0.0546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5635   -0.0955   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9886    0.4273   -1.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6509    0.7363   -1.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8736    0.5466   -0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4494    0.0262    1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937   -0.2916    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3396   -0.8188    2.1956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6966   -0.1863    2.2089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909   -0.0464    2.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1437    1.0873    1.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5876    0.9040    0.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7658    1.3114    1.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101    0.9763    1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0640    0.1982   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2961   -0.1562   -0.6123 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4941    0.2495   -0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892   -0.2264   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9458   -1.0101   -1.8414 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9772   -2.4138   -1.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6617    0.1272   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3582   -0.1792   -0.6081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600    0.8969   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3191    0.6997   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3907   -0.3777   -2.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6301   -1.0684   -1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5948    0.5865   -2.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2263    1.1507   -2.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3162   -1.0789    2.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1413    0.0465    3.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084   -0.9846    1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0808    2.0803    1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7009    1.9139    2.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9310    1.3081    1.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3505   -0.1142   -0.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6442   -0.1790    0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6142    1.3363    0.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5462   -2.9704   -2.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -2.7122   -0.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094   -2.7700   -1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2291    1.8102   -0.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 24 12  1  0
 24  6  1  0
 22 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 24 42  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      12.822  -2.132   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.531  -6.633   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.429  -7.592   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.353  -2.145   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.362  -5.059   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.899  -4.971   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.985  -2.851   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.827  -1.196   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.649  -2.978   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.517  -3.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.135  -2.572   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.592  -3.595   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.911  -4.389   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.979  -3.859   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.210  -2.396   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.576  -4.516   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.440  -0.932   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.129  -3.507   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.134  -6.760   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.365  -1.108   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.016  -5.061   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4    7    9                                                       
CONECT    5    6   10                                                       
CONECT    6    5   12                                                       
CONECT    7    4   13                                                       
CONECT    8   11   23                                                       
CONECT    9    4   11   17                                                  
CONECT   10    5   15   16                                                  
CONECT   11    8    9   15                                                  
CONECT   12    6   14   20                                                  
CONECT   13    7   18   21                                                  
CONECT   14   12   16   19                                                  
CONECT   15   10   11   24                                                  
CONECT   16   10   14   23                                                  
CONECT   17    9   18   24                                                  
CONECT   18   13   17   22                                                  
CONECT   19   14                                                            
CONECT   20    1   12                                                       
CONECT   21    2   13                                                       
CONECT   22    3   18                                                       
CONECT   23    8   16                                                       
CONECT   24   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0033697
HETATM    1  C1  UNL     1      -6.814  -0.303  -1.101  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.902  -0.436  -0.055  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.563  -0.095  -0.109  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.989   0.427  -1.248  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.651   0.736  -1.208  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.874   0.547  -0.090  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.449   0.026   1.041  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.794  -0.292   1.023  1.00  0.00           C  
HETATM    9  O2  UNL     1      -4.340  -0.819   2.196  1.00  0.00           O  
HETATM   10  O3  UNL     1      -1.697  -0.186   2.209  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.291  -0.046   2.146  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.144   1.087   1.250  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.588   0.904   0.966  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.766   1.311   1.552  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.010   0.976   1.052  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.064   0.198  -0.085  1.00  0.00           C  
HETATM   17  O4  UNL     1       5.296  -0.156  -0.612  1.00  0.00           O  
HETATM   18  C14 UNL     1       6.494   0.249  -0.029  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.889  -0.226  -0.696  1.00  0.00           C  
HETATM   20  O5  UNL     1       2.946  -1.010  -1.841  1.00  0.00           O  
HETATM   21  C16 UNL     1       2.977  -2.414  -1.651  1.00  0.00           C  
HETATM   22  C17 UNL     1       1.662   0.127  -0.170  1.00  0.00           C  
HETATM   23  O6  UNL     1       0.358  -0.179  -0.608  1.00  0.00           O  
HETATM   24  C18 UNL     1      -0.460   0.897  -0.118  1.00  0.00           C  
HETATM   25  H1  UNL     1      -7.319   0.700  -1.025  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.391  -0.378  -2.106  1.00  0.00           H  
HETATM   27  H3  UNL     1      -7.630  -1.068  -1.047  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.595   0.586  -2.153  1.00  0.00           H  
HETATM   29  H5  UNL     1      -2.226   1.151  -2.133  1.00  0.00           H  
HETATM   30  H6  UNL     1      -5.316  -1.079   2.269  1.00  0.00           H  
HETATM   31  H7  UNL     1       0.141   0.047   3.153  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.108  -0.985   1.705  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.081   2.080   1.681  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.701   1.914   2.433  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.931   1.308   1.530  1.00  0.00           H  
HETATM   36  H12 UNL     1       7.351  -0.114  -0.634  1.00  0.00           H  
HETATM   37  H13 UNL     1       6.644  -0.179   0.999  1.00  0.00           H  
HETATM   38  H14 UNL     1       6.614   1.336   0.078  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.546  -2.970  -2.493  1.00  0.00           H  
HETATM   40  H16 UNL     1       2.370  -2.712  -0.747  1.00  0.00           H  
HETATM   41  H17 UNL     1       4.009  -2.770  -1.436  1.00  0.00           H  
HETATM   42  H18 UNL     1      -0.229   1.810  -0.703  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   28
CONECT    5    6    6   29
CONECT    6    7   24
CONECT    7    8    8   10
CONECT    8    9
CONECT    9   30
CONECT   10   11
CONECT   11   12   31   32
CONECT   12   13   24   33
CONECT   13   14   14   22
CONECT   14   15   34
CONECT   15   16   16   35
CONECT   16   17   19
CONECT   17   18
CONECT   18   36   37   38
CONECT   19   20   22   22
CONECT   20   21
CONECT   21   39   40   41
CONECT   22   23
CONECT   23   24
CONECT   24   42
END

HMDB0033697
     RDKit          3D
Melilotocarpan C
 42 45  0  0  0  0  0  0  0  0999 V2000
   -6.8139   -0.3034   -1.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9018   -0.4364   -0.0546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5635   -0.0955   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9886    0.4273   -1.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6509    0.7363   -1.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8736    0.5466   -0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4494    0.0262    1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937   -0.2916    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3396   -0.8188    2.1956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6966   -0.1863    2.2089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909   -0.0464    2.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1437    1.0873    1.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5876    0.9040    0.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7658    1.3114    1.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101    0.9763    1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0640    0.1982   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2961   -0.1562   -0.6123 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4941    0.2495   -0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892   -0.2264   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9458   -1.0101   -1.8414 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9772   -2.4138   -1.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6617    0.1272   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3582   -0.1792   -0.6081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600    0.8969   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3191    0.6997   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3907   -0.3777   -2.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6301   -1.0684   -1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5948    0.5865   -2.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2263    1.1507   -2.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3162   -1.0789    2.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1413    0.0465    3.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084   -0.9846    1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0808    2.0803    1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7009    1.9139    2.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9310    1.3081    1.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3505   -0.1142   -0.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6442   -0.1790    0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6142    1.3363    0.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5462   -2.9704   -2.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -2.7122   -0.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094   -2.7700   -1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2291    1.8102   -0.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 24 12  1  0
 24  6  1  0
 22 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 24 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-3,9,10-trimethoxypterocarpan	HMDB

Chemical Formula

C₁₈H₁₈O₆

Average Molecular Weight

330.3319

Monoisotopic Molecular Weight

330.110338308

IUPAC Name

5,14,15-trimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-6-ol

Traditional Name

melilotocarpan C

CAS Registry Number

83013-82-5

SMILES

COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(OC)=C3OC)C1CO2

InChI Identifier

InChI=1S/C18H18O6/c1-20-12-6-5-10-15-11(8-23-16(10)14(12)19)9-4-7-13(21-2)18(22-3)17(9)24-15/h4-7,11,15,19H,8H2,1-3H3

InChI Key

ITMVICNONDPRSU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Isoflavan
Chromane
1-benzopyran
Benzopyran
Coumaran
Benzofuran
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070086 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033697)
Cell membrane (HMDB: HMDB0033697)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033697)

Source

Exogenous

Exogenous (HMDB: HMDB0033697)

Food

Food (HMDB: HMDB0033697)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0033697)
Fabaceae (HMDB: HMDB0033697)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033697)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	160 - 162.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	2.63	ALOGPS
logP	2.19	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.99 m³·mol⁻¹	ChemAxon
Polarizability	33.92 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	177.696	31661259
DarkChem	[M-H]-	175.66	31661259
DeepCCS	[M+H]+	180.629	30932474
DeepCCS	[M-H]-	178.271	30932474
DeepCCS	[M-2H]-	212.011	30932474
DeepCCS	[M+Na]+	187.238	30932474
AllCCS	[M+H]+	177.9	32859911
AllCCS	[M+H-H2O]+	174.6	32859911
AllCCS	[M+NH4]+	181.0	32859911
AllCCS	[M+Na]+	181.9	32859911
AllCCS	[M-H]-	182.4	32859911
AllCCS	[M+Na-2H]-	182.0	32859911
AllCCS	[M+HCOO]-	181.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.26 minutes	32390414
Predicted by Siyang on May 30, 2022	12.261 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.7 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2067.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	247.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	105.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	545.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	568.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	145.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1075.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	425.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1249.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	371.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	361.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	357.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	342.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	28.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Melilotocarpan C	COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(OC)=C3OC)C1CO2	4030.7	Standard polar	33892256
Melilotocarpan C	COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(OC)=C3OC)C1CO2	2654.1	Standard non polar	33892256
Melilotocarpan C	COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(OC)=C3OC)C1CO2	2808.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Melilotocarpan C,1TMS,isomer #1	COC1=CC=C2C(=C1OC)OC1C3=CC=C(OC)C(O[Si](C)(C)C)=C3OCC21	2802.4	Semi standard non polar	33892256
Melilotocarpan C,1TBDMS,isomer #1	COC1=CC=C2C(=C1OC)OC1C3=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3OCC21	3029.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Melilotocarpan C GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gds-0978000000-610ecbb313dee5967c96	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melilotocarpan C GC-MS (1 TMS) - 70eV, Positive	splash10-059i-1119000000-912a0c126893b31f86fa	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Melilotocarpan C GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan C 10V, Positive-QTOF	splash10-001r-0509000000-bb7ffa35bbdd8fd87b09	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan C 20V, Positive-QTOF	splash10-001r-0529000000-8c23b453065e309d26f9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan C 40V, Positive-QTOF	splash10-001r-8910000000-846e39b16e5b4b2d0700	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan C 10V, Negative-QTOF	splash10-004i-0009000000-679b2a6c1d88d096a27c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan C 20V, Negative-QTOF	splash10-01t9-0069000000-e06f333cba67c6e7dabf	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan C 40V, Negative-QTOF	splash10-0bwc-0590000000-17b6466b7b708d678059	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan C 10V, Negative-QTOF	splash10-004i-0009000000-de11969ae6615b28f3d7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan C 20V, Negative-QTOF	splash10-01t9-0069000000-8a71d83566d4d9d77d38	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan C 40V, Negative-QTOF	splash10-001r-0490000000-6fcbded18045ac10fc6e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan C 10V, Positive-QTOF	splash10-001i-0009000000-2160799bc7c624fd0646	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan C 20V, Positive-QTOF	splash10-001i-0209000000-74502a999173be6d568c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotocarpan C 40V, Positive-QTOF	splash10-004l-0921000000-d3e954f571fba32b2710	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011807

KNApSAcK ID

C00010000

Chemspider ID

4477661

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319350

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Melilotocarpan C → 3,4,5-trihydroxy-6-({5,14,15-trimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-6-yl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for Melilotocarpan C (HMDB0033697)

MOL for HMDB0033697 (Melilotocarpan C)

3D MOL for HMDB0033697 (Melilotocarpan C)

3D SDF for HMDB0033697 (Melilotocarpan C)

3D-SDF for HMDB0033697 (Melilotocarpan C)

PDB for HMDB0033697 (Melilotocarpan C)

3D PDB for HMDB0033697 (Melilotocarpan C)

SMILES for HMDB0033697 (Melilotocarpan C)

INCHI for HMDB0033697 (Melilotocarpan C)

Structure for HMDB0033697 (Melilotocarpan C)

3D Structure for HMDB0033697 (Melilotocarpan C)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions