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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:56:27 UTC

Update Date

2023-02-21 17:24:57 UTC

HMDB ID

HMDB0035894

Secondary Accession Numbers

HMDB35894

Metabolite Identification

Common Name

(Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole

Description

(Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms (Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole has been detected, but not quantified in, herbs and spices. This could make (Z)-4-methoxy-6-(1-propenyl)-1,3-benzodioxole a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole.

Structure

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


  Mrv0541 05061308462D          

 14 15  0  0  0  0            999 V2000
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  2  0  0  0  0
  8  4  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12  2  1  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035894

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2OCOC2=CC(\C=C/C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O3/c1-3-4-8-5-9(12-2)11-10(6-8)13-7-14-11/h3-6H,7H2,1-2H3/b4-3-

> <INCHI_KEY>
DHUZAAUGHUHIDS-ARJAWSKDSA-N

> <FORMULA>
C11H12O3

> <MOLECULAR_WEIGHT>
192.2112

> <EXACT_MASS>
192.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.48021461002645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-6-[(1Z)-prop-1-en-1-yl]-2H-1,3-benzodioxole

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.562145080666667

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.539030515253374

> <JCHEM_POLAR_SURFACE_AREA>
27.69

> <JCHEM_REFRACTIVITY>
53.647900000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-6-[(1Z)-prop-1-en-1-yl]-2H-1,3-benzodioxole

> <JCHEM_VEBER_RULE>
1

$$$$

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       6.258   6.693   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258  -1.007   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   12                                                            
CONECT    3    1    4                                                       
CONECT    4    3    8                                                       
CONECT    5    8    9                                                       
CONECT    6    8   10                                                       
CONECT    7   13   14                                                       
CONECT    8    4    5    6                                                  
CONECT    9    5   11   12                                                  
CONECT   10    6   11   13                                                  
CONECT   11    9   10   14                                                  
CONECT   12    2    9                                                       
CONECT   13    7   10                                                       
CONECT   14    7   11                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0035894
HETATM    1  C1  UNL     1       3.650  -0.432  -0.513  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.298   0.676   0.379  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.058   0.959   0.626  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.856   0.333   0.155  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.375   1.017   0.318  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.579   0.534  -0.034  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.757   1.225   0.138  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.883   2.500   0.688  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.630  -0.724  -0.597  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.505  -1.464  -0.795  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.719  -0.905  -0.407  1.00  0.00           C  
HETATM   12  O2  UNL     1      -0.849  -2.678  -1.372  1.00  0.00           O  
HETATM   13  C11 UNL     1      -2.238  -2.844  -1.201  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.693  -1.510  -1.067  1.00  0.00           O  
HETATM   15  H1  UNL     1       4.752  -0.208  -0.805  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.158  -0.399  -1.517  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.728  -1.417  -0.059  1.00  0.00           H  
HETATM   18  H4  UNL     1       4.104   1.292   0.860  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.897   1.824   1.325  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.318   2.002   0.758  1.00  0.00           H  
HETATM   21  H7  UNL     1      -2.646   3.316  -0.032  1.00  0.00           H  
HETATM   22  H8  UNL     1      -2.234   2.552   1.597  1.00  0.00           H  
HETATM   23  H9  UNL     1      -3.926   2.609   1.055  1.00  0.00           H  
HETATM   24  H10 UNL     1       1.564  -1.529  -0.546  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.499  -3.477  -0.333  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.654  -3.251  -2.163  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3   18
CONECT    3    4   19
CONECT    4    5    5   11
CONECT    5    6   20
CONECT    6    7    9    9
CONECT    7    8
CONECT    8   21   22   23
CONECT    9   10   14
CONECT   10   11   11   12
CONECT   11   24
CONECT   12   13
CONECT   13   14   25   26
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂O₃

Average Molecular Weight

192.2112

Monoisotopic Molecular Weight

192.07864425

IUPAC Name

4-methoxy-6-[(1Z)-prop-1-en-1-yl]-2H-1,3-benzodioxole

Traditional Name

4-methoxy-6-[(1Z)-prop-1-en-1-yl]-2H-1,3-benzodioxole

CAS Registry Number

Not Available

SMILES

COC1=C2OCOC2=CC(\C=C/C)=C1

InChI Identifier

InChI=1S/C11H12O3/c1-3-4-8-5-9(12-2)11-10(6-8)13-7-14-11/h3-6H,7H2,1-2H3/b4-3-

InChI Key

DHUZAAUGHUHIDS-ARJAWSKDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Styrene
Anisole
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0035894)
Cell membrane (HMDB: HMDB0035894)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035894)

Source

Exogenous

Exogenous (HMDB: HMDB0035894)

Food

Food (HMDB: HMDB0035894)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0035894)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035894)

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
Water Solubility	0.44 g/L	ALOGPS
logP	2.68	ALOGPS
logP	2.56	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	53.65 m³·mol⁻¹	ChemAxon
Polarizability	20.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	148.121	31661259
DarkChem	[M-H]-	144.399	31661259
DeepCCS	[M+H]+	142.976	30932474
DeepCCS	[M-H]-	140.378	30932474
DeepCCS	[M-2H]-	176.145	30932474
DeepCCS	[M+Na]+	150.982	30932474
AllCCS	[M+H]+	139.7	32859911
AllCCS	[M+H-H2O]+	135.3	32859911
AllCCS	[M+NH4]+	143.8	32859911
AllCCS	[M+Na]+	145.0	32859911
AllCCS	[M-H]-	142.3	32859911
AllCCS	[M+Na-2H]-	142.5	32859911
AllCCS	[M+HCOO]-	142.9	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.	6.41 minutes	32390414
Predicted by Siyang on May 30, 2022	14.6461 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.05 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2148.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	469.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	184.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	287.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	132.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	563.6 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	654.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	124.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1276.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	462.2 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	1308.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	417.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	375.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	453.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	493.6 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	27.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole	COC1=C2OCOC2=CC(\C=C/C)=C1	2417.1	Standard polar	33892256
(Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole	COC1=C2OCOC2=CC(\C=C/C)=C1	1522.3	Standard non polar	33892256
(Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole	COC1=C2OCOC2=CC(\C=C/C)=C1	1633.1	Semi standard non polar	33892256

Spectra

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

FDB014679

KNApSAcK ID

Not Available

Chemspider ID

30777147

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91748544

PDB ID

Not Available

ChEBI ID

173924

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.. .

Showing metabocard for (Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole (HMDB0035894)

MOL for HMDB0035894 ((Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole)

3D MOL for HMDB0035894 ((Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole)

3D SDF for HMDB0035894 ((Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole)

3D-SDF for HMDB0035894 ((Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole)

PDB for HMDB0035894 ((Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole)

3D PDB for HMDB0035894 ((Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole)

SMILES for HMDB0035894 ((Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole)

INCHI for HMDB0035894 ((Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole)

Structure for HMDB0035894 ((Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole)

3D Structure for HMDB0035894 ((Z)-4-Methoxy-6-(1-propenyl)-1,3-benzodioxole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized