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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 22:00:27 UTC

Update Date

2021-09-23 22:00:27 UTC

HMDB ID

HMDB0302945

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+)-Royleanone

Description

(4bS,8aS)-3-hydroxy-4b,8,8-trimethyl-2-(propan-2-yl)-1,4,4b,5,6,7,8,8a,9,10-decahydrophenanthrene-1,4-dione belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review very few articles have been published on (4bS,8aS)-3-hydroxy-4b,8,8-trimethyl-2-(propan-2-yl)-1,4,4b,5,6,7,8,8a,9,10-decahydrophenanthrene-1,4-dione.

Structure

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

HMDB0302945
     RDKit          3D
(+)-Royleanone
 51 53  0  0  0  0  0  0  0  0999 V2000
    4.8506   -1.3706   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5738   -0.0775    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4443    0.9804   -0.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1519    0.2361    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5907    1.3499   -0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3957    2.3418   -0.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1534    1.6132   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6741    2.6969   -0.4397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3101    0.5682    0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8193   -0.6042    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0383   -1.6962    1.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3041   -1.8317    0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7057   -0.5649    0.0071 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1283   -0.4939   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1509   -0.5972    0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3380   -1.7250   -1.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3888    0.6941   -1.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2659    1.7028   -1.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8302    1.8742    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569    0.6752    0.6825 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4169    0.6640    2.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2604   -0.7771    0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7216   -1.8990    1.2342 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1703   -1.4683   -1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644   -2.2566    0.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8932   -1.3463   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9239   -0.2673    1.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5010    0.5764   -0.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5016    1.9124    0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2630    1.1796   -1.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1183    2.8676   -1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5786   -2.6410    1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1677   -1.6454    2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1601   -2.6651   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1028   -2.1676    1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1294   -0.5821   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9053   -1.2406    1.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5717    0.3949    0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0641   -1.0821    0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2489   -2.5972   -0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -1.6990   -1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934   -1.8100   -2.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2914    1.2492   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326    0.4411   -2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885    2.6775   -1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4463    1.4279   -1.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8480    1.9889    0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3841    2.8555    0.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9750    1.5930    2.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4846    0.7050    2.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0235   -0.1598    2.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 10 22  1  0
 22 23  2  0
 22  4  1  0
 20  9  1  0
 20 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  6 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  6
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
M  END


  Mrv0541 02241212582D          

 24 26  0  0  0  0            999 V2000
   -4.1545    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8689   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8689   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1545   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4400   -1.0313    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4400   -0.2062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7255    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7255   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7255    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670   -2.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7420   -2.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -1.6795    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4400    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4400    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
  7 10  2  0  0  0  0
 12  7  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  2  0  0  0  0
 13 14  1  0  0  0  0
  4 15  1  0  0  0  0
  4 16  1  0  0  0  0
  5 17  1  6  0  0  0
  6 18  1  1  0  0  0
 13 19  2  0  0  0  0
 12 20  2  0  0  0  0
 11 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302945

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCC3=C(C(=O)C(O)=C(C(C)C)C3=O)[C@@]1(C)CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-11(2)14-16(21)12-7-8-13-19(3,4)9-6-10-20(13,5)15(12)18(23)17(14)22/h11,13,22H,6-10H2,1-5H3/t13-,20-/m0/s1

> <INCHI_KEY>
KZAPVZIQILABNM-RBZFPXEDSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.4345

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.49406686430704

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4bS,8aS)-3-hydroxy-4b,8,8-trimethyl-2-(propan-2-yl)-1,4,4b,5,6,7,8,8a,9,10-decahydrophenanthrene-1,4-dione

> <ALOGPS_LOGP>
3.95

> <JCHEM_LOGP>
4.735669743000001

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.772144308391734

> <JCHEM_PKA_STRONGEST_BASIC>
-3.891324079509455

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
92.61269999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
royleanone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302945
     RDKit          3D
(+)-Royleanone
 51 53  0  0  0  0  0  0  0  0999 V2000
    4.8506   -1.3706   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5738   -0.0775    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4443    0.9804   -0.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1519    0.2361    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5907    1.3499   -0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3957    2.3418   -0.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1534    1.6132   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6741    2.6969   -0.4397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3101    0.5682    0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8193   -0.6042    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0383   -1.6962    1.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3041   -1.8317    0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7057   -0.5649    0.0071 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1283   -0.4939   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1509   -0.5972    0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3380   -1.7250   -1.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3888    0.6941   -1.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2659    1.7028   -1.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8302    1.8742    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569    0.6752    0.6825 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4169    0.6640    2.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2604   -0.7771    0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7216   -1.8990    1.2342 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1703   -1.4683   -1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644   -2.2566    0.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8932   -1.3463   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9239   -0.2673    1.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5010    0.5764   -0.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5016    1.9124    0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2630    1.1796   -1.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1183    2.8676   -1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5786   -2.6410    1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1677   -1.6454    2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1601   -2.6651   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1028   -2.1676    1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1294   -0.5821   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9053   -1.2406    1.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5717    0.3949    0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0641   -1.0821    0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2489   -2.5972   -0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -1.6990   -1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934   -1.8100   -2.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2914    1.2492   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326    0.4411   -2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885    2.6775   -1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4463    1.4279   -1.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8480    1.9889    0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3841    2.8555    0.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9750    1.5930    2.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4846    0.7050    2.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0235   -0.1598    2.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 10 22  1  0
 22 23  2  0
 22  4  1  0
 20  9  1  0
 20 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  6 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  6
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.755   0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.089  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.089  -1.925   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.755  -2.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.421  -1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.421  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.088   0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.088  -2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.754  -1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.754  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.754   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.088   1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.420   0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.420   1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.525  -4.029   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.985  -4.029   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      -6.366  -3.135   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0      -6.421   1.155   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.087  -0.385   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -6.421   2.695   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -3.754   4.235   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.087   2.695   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.247   1.925   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.087   4.235   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   15   16                                             
CONECT    5    4    6    8   17                                             
CONECT    6    1    7    5   18                                             
CONECT    7    6   10   12                                                  
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   13    7                                                  
CONECT   11   12   14   21                                                  
CONECT   12    7   11   20                                                  
CONECT   13   10   14   19                                                  
CONECT   14   11   13   22                                                  
CONECT   15    4                                                            
CONECT   16    4                                                            
CONECT   17    5                                                            
CONECT   18    6                                                            
CONECT   19   13                                                            
CONECT   20   12                                                            
CONECT   21   11                                                            
CONECT   22   14   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0302945
HETATM    1  C1  UNL     1       4.851  -1.371  -0.548  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.574  -0.077   0.204  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.444   0.980  -0.367  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.152   0.236   0.267  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.591   1.350  -0.130  1.00  0.00           C  
HETATM    6  O1  UNL     1       3.396   2.342  -0.664  1.00  0.00           O  
HETATM    7  C6  UNL     1       1.153   1.613  -0.043  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.674   2.697  -0.440  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.310   0.568   0.519  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.819  -0.604   0.946  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.038  -1.696   1.514  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.304  -1.832   0.708  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.706  -0.565   0.007  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.128  -0.494  -0.414  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.151  -0.597   0.654  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.338  -1.725  -1.326  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.389   0.694  -1.286  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.266   1.703  -1.310  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.830   1.874   0.146  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.157   0.675   0.683  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.417   0.664   2.184  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.260  -0.777   0.821  1.00  0.00           C  
HETATM   23  O3  UNL     1       2.722  -1.899   1.234  1.00  0.00           O  
HETATM   24  H1  UNL     1       4.170  -1.468  -1.427  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.764  -2.257   0.124  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.893  -1.346  -0.911  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.924  -0.267   1.254  1.00  0.00           H  
HETATM   28  H5  UNL     1       6.501   0.576  -0.337  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.502   1.912   0.244  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.263   1.180  -1.443  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.118   2.868  -1.483  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.579  -2.641   1.377  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.168  -1.645   2.594  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.160  -2.665  -0.011  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.103  -2.168   1.399  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.129  -0.582  -0.974  1.00  0.00           H  
HETATM   37  H14 UNL     1      -3.905  -1.241   1.509  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.572   0.395   0.987  1.00  0.00           H  
HETATM   39  H16 UNL     1      -5.064  -1.082   0.189  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.249  -2.597  -0.640  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.319  -1.699  -1.804  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.493  -1.810  -2.050  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.291   1.249  -0.904  1.00  0.00           H  
HETATM   44  H21 UNL     1      -3.633   0.441  -2.336  1.00  0.00           H  
HETATM   45  H22 UNL     1      -2.689   2.678  -1.620  1.00  0.00           H  
HETATM   46  H23 UNL     1      -1.446   1.428  -1.968  1.00  0.00           H  
HETATM   47  H24 UNL     1      -2.848   1.989   0.664  1.00  0.00           H  
HETATM   48  H25 UNL     1      -1.384   2.856   0.360  1.00  0.00           H  
HETATM   49  H26 UNL     1      -1.975   1.593   2.512  1.00  0.00           H  
HETATM   50  H27 UNL     1      -0.485   0.705   2.782  1.00  0.00           H  
HETATM   51  H28 UNL     1      -2.024  -0.160   2.528  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4   27
CONECT    3   28   29   30
CONECT    4    5    5   22
CONECT    5    6    7
CONECT    6   31
CONECT    7    8    8    9
CONECT    9   10   10   20
CONECT   10   11   22
CONECT   11   12   32   33
CONECT   12   13   34   35
CONECT   13   14   20   36
CONECT   14   15   16   17
CONECT   15   37   38   39
CONECT   16   40   41   42
CONECT   17   18   43   44
CONECT   18   19   45   46
CONECT   19   20   47   48
CONECT   20   21
CONECT   21   49   50   51
CONECT   22   23   23
END

HMDB0302945
     RDKit          3D
(+)-Royleanone
 51 53  0  0  0  0  0  0  0  0999 V2000
    4.8506   -1.3706   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5738   -0.0775    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4443    0.9804   -0.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1519    0.2361    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5907    1.3499   -0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3957    2.3418   -0.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1534    1.6132   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6741    2.6969   -0.4397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3101    0.5682    0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8193   -0.6042    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0383   -1.6962    1.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3041   -1.8317    0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7057   -0.5649    0.0071 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1283   -0.4939   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1509   -0.5972    0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3380   -1.7250   -1.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3888    0.6941   -1.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2659    1.7028   -1.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8302    1.8742    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569    0.6752    0.6825 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4169    0.6640    2.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2604   -0.7771    0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7216   -1.8990    1.2342 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1703   -1.4683   -1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644   -2.2566    0.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8932   -1.3463   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9239   -0.2673    1.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5010    0.5764   -0.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5016    1.9124    0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2630    1.1796   -1.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1183    2.8676   -1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5786   -2.6410    1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1677   -1.6454    2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1601   -2.6651   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1028   -2.1676    1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1294   -0.5821   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9053   -1.2406    1.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5717    0.3949    0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0641   -1.0821    0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2489   -2.5972   -0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -1.6990   -1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934   -1.8100   -2.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2914    1.2492   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326    0.4411   -2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885    2.6775   -1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4463    1.4279   -1.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8480    1.9889    0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3841    2.8555    0.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9750    1.5930    2.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4846    0.7050    2.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0235   -0.1598    2.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 10 22  1  0
 22 23  2  0
 22  4  1  0
 20  9  1  0
 20 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  6 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  6
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.4345

Monoisotopic Molecular Weight

316.203844762

IUPAC Name

(4bS,8aS)-3-hydroxy-4b,8,8-trimethyl-2-(propan-2-yl)-1,4,4b,5,6,7,8,8a,9,10-decahydrophenanthrene-1,4-dione

Traditional Name

royleanone

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC3=C(C(=O)C(O)=C(C(C)C)C3=O)[C@@]1(C)CCCC2(C)C

InChI Identifier

InChI=1S/C20H28O3/c1-11(2)14-16(21)12-7-8-13-19(3,4)9-6-10-20(13,5)15(12)18(23)17(14)22/h11,13,22H,6-10H2,1-5H3/t13-,20-/m0/s1

InChI Key

KZAPVZIQILABNM-RBZFPXEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Abietane diterpenoid
Phenanthrene
Hydrophenanthrene
Vinylogous acid
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

diterpenoid (CHEBI:8904 )
Abietanes (C09182 )

Ontology

Not Available

Exogenous (HMDB: HMDB0302945)

Food

Herb and spice

Herb

Common sage (FooDB: FOOD00165)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	3.95	ALOGPS
logP	4.74	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.77	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.61 m³·mol⁻¹	ChemAxon
Polarizability	36.49 Å³	ChemAxon
Number of Rings	3	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
AllCCS	[M+H]+	175.904	32859911
AllCCS	[M+H-H2O]+	172.902	32859911
AllCCS	[M+Na]+	179.479	32859911
AllCCS	[M+NH4]+	178.681	32859911
AllCCS	[M-H]-	185.807	32859911
AllCCS	[M+Na-2H]-	186.19	32859911
AllCCS	[M+HCOO]-	186.748	32859911
DeepCCS	[M-2H]-	220.379	30932474
DeepCCS	[M+Na]+	195.39	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	17.7205 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.91 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2500.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	240.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	192.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	108.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	551.7 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	613.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	109.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1034.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	454.6 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	1369.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	337.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	301.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	366.9 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	15.7 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Royleanone 10V, Positive-QTOF	splash10-014i-0259000000-b6656115454bdfe78a10	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Royleanone 20V, Positive-QTOF	splash10-016r-2593000000-5f1c130a9a96eee3abd0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Royleanone 40V, Positive-QTOF	splash10-0kmr-4920000000-866b25a2bb2054eb3351	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Royleanone 10V, Negative-QTOF	splash10-014i-0019000000-4681e0017049a767599c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Royleanone 20V, Negative-QTOF	splash10-014i-0159000000-1eab2fe9dfedb199a7a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Royleanone 40V, Negative-QTOF	splash10-0udj-2590000000-91eb79f9e27a7015adfb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Royleanone 10V, Positive-QTOF	splash10-014i-0009000000-3cdabe8d2eed9a772531	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Royleanone 20V, Positive-QTOF	splash10-014i-0398000000-4369d923536ca3ae7c44	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Royleanone 40V, Positive-QTOF	splash10-0a4i-8970000000-4968600b2c0b8f8d87b0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Royleanone 10V, Negative-QTOF	splash10-014i-0009000000-d337ec43015bf5d00be6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Royleanone 20V, Negative-QTOF	splash10-014i-0139000000-d797c25a042df1c9e0aa	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Royleanone 40V, Negative-QTOF	splash10-0bta-2192000000-254d6a1bc22bea276482	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

8904

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

Not Available

Showing metabocard for (+)-Royleanone (HMDB0302945)

MOL for HMDB0302945 ((+)-Royleanone)

3D MOL for HMDB0302945 ((+)-Royleanone)

3D SDF for HMDB0302945 ((+)-Royleanone)

3D-SDF for HMDB0302945 ((+)-Royleanone)

PDB for HMDB0302945 ((+)-Royleanone)

3D PDB for HMDB0302945 ((+)-Royleanone)

SMILES for HMDB0302945 ((+)-Royleanone)

INCHI for HMDB0302945 ((+)-Royleanone)

Structure for HMDB0302945 ((+)-Royleanone)

3D Structure for HMDB0302945 ((+)-Royleanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra