MiMeDB: Showing metabocard for Methyl 3-(4,5,6,8,8a,9-hexahydro-4-((E)-3-methylpent-1-enyl)-4H-furo[3,2-g]isochromen-6-yl)propanoate (MMDBc0023537)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 13:30:56 UTC

Update Date

2022-08-31 06:48:37 UTC

Metabolite ID

MMDBc0023537

Metabolite Identification

Common Name

Methyl 3-(4,5,6,8,8a,9-hexahydro-4-((E)-3-methylpent-1-enyl)-4H-furo[3,2-g]isochromen-6-yl)propanoate

Description

Methyl 3-(4,5,6,8,8a,9-hexahydro-4-((E)-3-methylpent-1-enyl)-4H-furo[3,2-g]isochromen-6-yl)propanoate belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Methyl 3-(4,5,6,8,8a,9-hexahydro-4-((E)-3-methylpent-1-enyl)-4H-furo[3,2-g]isochromen-6-yl)propanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152115302D          

 32 34  0  0  1  0            999 V2000
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3570   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8419   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3570    0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
 10  9  2  0  0  0  0
 14  2  1  0  0  0  0
 14  4  1  0  0  0  0
 14  5  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16  6  1  1  0  0  0
 16 12  1  0  0  0  0
 17  7  1  1  0  0  0
 18  9  1  0  0  0  0
 18 17  1  0  0  0  0
 19 12  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20 11  1  0  0  0  0
 20 18  2  0  0  0  0
 21  8  1  0  0  0  0
 22 21  2  0  0  0  0
 23  3  1  0  0  0  0
 23 21  1  0  0  0  0
 24 10  1  0  0  0  0
 24 20  1  0  0  0  0
 25 13  1  0  0  0  0
 25 16  1  0  0  0  0
 26  5  1  0  0  0  0
 27  7  1  0  0  0  0
 28 14  1  0  0  0  0
 15 29  1  1  0  0  0
 16 30  1  6  0  0  0
 17 31  1  6  0  0  0
 19 32  1  6  0  0  0
M  END


  Mrv1652305152115302D          

 32 34  0  0  1  0            999 V2000
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3570   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8419   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3570    0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
 10  9  2  0  0  0  0
 14  2  1  0  0  0  0
 14  4  1  0  0  0  0
 14  5  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16  6  1  1  0  0  0
 16 12  1  0  0  0  0
 17  7  1  1  0  0  0
 18  9  1  0  0  0  0
 18 17  1  0  0  0  0
 19 12  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20 11  1  0  0  0  0
 20 18  2  0  0  0  0
 21  8  1  0  0  0  0
 22 21  2  0  0  0  0
 23  3  1  0  0  0  0
 23 21  1  0  0  0  0
 24 10  1  0  0  0  0
 24 20  1  0  0  0  0
 25 13  1  0  0  0  0
 25 16  1  0  0  0  0
 26  5  1  0  0  0  0
 27  7  1  0  0  0  0
 28 14  1  0  0  0  0
 15 29  1  1  0  0  0
 16 30  1  6  0  0  0
 17 31  1  6  0  0  0
 19 32  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0023537

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])[C@@]1([H])C2=C(C[C@]3([H])CO[C@@]([H])(CCC(=O)OC)C[C@@]13[H])OC=C2)C([H])(C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O4/c1-4-14(2)5-7-17-18-9-10-24-20(18)11-15-13-25-16(12-19(15)17)6-8-21(22)23-3/h5,7,9-10,14-17,19H,4,6,8,11-13H2,1-3H3/b7-5+/t14?,15-,16+,17+,19-/m1/s1

> <INCHI_KEY>
LBBXLAVURLOGQS-OVHXUYRLSA-N

> <FORMULA>
C21H30O4

> <MOLECULAR_WEIGHT>
346.467

> <EXACT_MASS>
346.214409446

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.08124859553444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3-[(1S,8R,9S,11S)-8-[(1E)-3-methylpent-1-en-1-yl]-4,12-dioxatricyclo[7.4.0.0^{3,7}]trideca-3(7),5-dien-11-yl]propanoate

> <ALOGPS_LOGP>
4.75

> <JCHEM_LOGP>
3.9144557043333323

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8027549428344924

> <JCHEM_POLAR_SURFACE_AREA>
48.67

> <JCHEM_REFRACTIVITY>
98.6497

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-[(1S,8R,9S,11S)-8-[(1E)-3-methylpent-1-en-1-yl]-4,12-dioxatricyclo[7.4.0.0^{3,7}]trideca-3(7),5-dien-11-yl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002  -6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.133  -1.246   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.038  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.668   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -8.133   1.246   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.334   0.770   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0      -8.002  -3.080   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.001  -3.850   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      -6.668  -6.930   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.667  -0.000   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.000  -0.000   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.001  -2.310   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.335  -0.000   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   14                                                            
CONECT    3   23                                                            
CONECT    4    1   14                                                       
CONECT    5    7   14   26                                                  
CONECT    6    8   16                                                       
CONECT    7    5   17   27                                                  
CONECT    8    6   21                                                       
CONECT    9   10   18                                                       
CONECT   10    9   24                                                       
CONECT   11   15   20                                                       
CONECT   12   16   19                                                       
CONECT   13   15   25                                                       
CONECT   14    2    4    5   28                                             
CONECT   15   11   13   19   29                                             
CONECT   16    6   12   25   30                                             
CONECT   17    7   18   19   31                                             
CONECT   18    9   17   20                                                  
CONECT   19   12   15   17   32                                             
CONECT   20   11   18   24                                                  
CONECT   21    8   22   23                                                  
CONECT   22   21                                                            
CONECT   23    3   21                                                       
CONECT   24   10   20                                                       
CONECT   25   13   16                                                       
CONECT   26    5                                                            
CONECT   27    7                                                            
CONECT   28   14                                                            
CONECT   29   15                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
CONECT   32   19                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

Synonyms

Value	Source
Methyl 3-(4,5,6,8,8a,9-hexahydro-4-((e)-3-methylpent-1-enyl)-4H-furo[3,2-g]isochromen-6-yl)propanoic acid	Generator

Molecular Formula

C₂₁H₃₀O₄

Average Mass

346.467

Monoisotopic Mass

346.214409446

IUPAC Name

methyl 3-[(1S,8R,9S,11S)-8-[(1E)-3-methylpent-1-en-1-yl]-4,12-dioxatricyclo[7.4.0.0^{3,7}]trideca-3(7),5-dien-11-yl]propanoate

Traditional Name

methyl 3-[(1S,8R,9S,11S)-8-[(1E)-3-methylpent-1-en-1-yl]-4,12-dioxatricyclo[7.4.0.0^{3,7}]trideca-3(7),5-dien-11-yl]propanoate

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])[C@@]1([H])C2=C(C[C@]3([H])CO[C@@]([H])(CCC(=O)OC)C[C@@]13[H])OC=C2)C([H])(C)CC

InChI Identifier

InChI=1S/C21H30O4/c1-4-14(2)5-7-17-18-9-10-24-20(18)11-15-13-25-16(12-19(15)17)6-8-21(22)23-3/h5,7,9-10,14-17,19H,4,6,8,11-13H2,1-3H3/b7-5+/t14?,15-,16+,17+,19-/m1/s1

InChI Key

LBBXLAVURLOGQS-OVHXUYRLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Fatty acid ester
Fatty acyl
Oxane
Heteroaromatic compound
Methyl ester
Furan
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0062 g/L	ALOGPS
logP	4.75	ALOGPS
logP	3.91	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	98.65 m³·mol⁻¹	ChemAxon
Polarizability	40.08 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	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	2	Human ; Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78442233

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139590857

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Methyl 3-(4,5,6,8,8a,9-hexahydro-4-((E)-3-methylpent-1-enyl)-4H-furo[3,2-g]isochromen-6-yl)propanoate (MMDBc0023537)

MOL for #<Metabolite:0x00007feccc0c5d58>

3D MOL for #<Metabolite:0x00007feccc0c5d58>

3D SDF for #<Metabolite:0x00007feccc0c5d58>

3D-SDF for #<Metabolite:0x00007feccc0c5d58>

PDB for #<Metabolite:0x00007feccc0c5d58>

3D PDB for #<Metabolite:0x00007feccc0c5d58>

SMILES for #<Metabolite:0x00007feccc0c5d58>

INCHI for #<Metabolite:0x00007feccc0c5d58>

Structure for #<Metabolite:0x00007feccc0c5d58>

3D Structure for #<Metabolite:0x00007feccc0c5d58>