NP-MRD: Showing NP-Card for (7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate (NP0335784)

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Record Information

Version

2.0

Created at

2024-09-11 03:13:17 UTC

Updated at

2024-09-11 03:13:18 UTC

NP-MRD ID

NP0335784

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate

Description

(7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Based on a literature review very few articles have been published on (7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262305452D          

 28 30  0  0  0  0            999 V2000
   -3.9284    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -0.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    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
 12  4  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  2  0  0  0  0
 14  8  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16  6  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  2  0  0  0  0
 18  9  2  0  0  0  0
 19  7  1  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
 21 14  2  0  0  0  0
 21 18  1  0  0  0  0
 22 11  1  0  0  0  0
 23 16  1  0  0  0  0
 24 19  2  0  0  0  0
 25  1  1  0  0  0  0
 25 17  1  0  0  0  0
 26  2  1  0  0  0  0
 26 18  1  0  0  0  0
 27  3  1  0  0  0  0
 27 19  1  0  0  0  0
 28 20  1  0  0  0  0
 28 21  1  0  0  0  0
M  END


  Mrv2104 05262305452D          

 28 30  0  0  0  0            999 V2000
   -3.9284    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -0.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    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
 12  4  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  2  0  0  0  0
 14  8  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16  6  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  2  0  0  0  0
 18  9  2  0  0  0  0
 19  7  1  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
 21 14  2  0  0  0  0
 21 18  1  0  0  0  0
 22 11  1  0  0  0  0
 23 16  1  0  0  0  0
 24 19  2  0  0  0  0
 25  1  1  0  0  0  0
 25 17  1  0  0  0  0
 26  2  1  0  0  0  0
 26 18  1  0  0  0  0
 27  3  1  0  0  0  0
 27 19  1  0  0  0  0
 28 20  1  0  0  0  0
 28 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335784

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C/C1=CC2=C(OC(C2CO)C2=CC(OC)=C(O)C=C2)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1/C21H22O7/c1-25-17-10-13(5-6-16(17)23)20-15(11-22)14-8-12(4-7-19(24)27-3)9-18(26-2)21(14)28-20/h4-10,15,20,22-23H,11H2,1-3H3/b7-4-

> <INCHI_KEY>
DPDJZJNYBSGDHT-DAXSKMNVNA-N

> <FORMULA>
C21H22O7

> <MOLECULAR_WEIGHT>
386.4

> <EXACT_MASS>
386.136553048

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
40.07070410912182

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2Z)-3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate

> <JCHEM_LOGP>
2.5327141609999995

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.190466351241412

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.909972249848655

> <JCHEM_PKA_STRONGEST_BASIC>
-2.715491027378465

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
103.09339999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2Z)-3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -7.333   0.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.197   6.693   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.865   5.923   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.483   4.176   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.023   4.176   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.744   0.132   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.793   2.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.023   1.509   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.250  -0.188   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -7.333   2.843   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -5.793   0.175   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       7.865   4.383   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
CONECT    1   25                                                            
CONECT    2   26                                                            
CONECT    3   27                                                            
CONECT    4    7   12                                                       
CONECT    5    6   13                                                       
CONECT    6    5   16                                                       
CONECT    7    4   19                                                       
CONECT    8   12   14                                                       
CONECT    9   12   18                                                       
CONECT   10   13   17                                                       
CONECT   11   15   22                                                       
CONECT   12    4    8    9                                                  
CONECT   13    5   10   20                                                  
CONECT   14    8   15   21                                                  
CONECT   15   11   14   20                                                  
CONECT   16    6   17   23                                                  
CONECT   17   10   16   25                                                  
CONECT   18    9   21   26                                                  
CONECT   19    7   24   27                                                  
CONECT   20   13   15   28                                                  
CONECT   21   14   18   28                                                  
CONECT   22   11                                                            
CONECT   23   16                                                            
CONECT   24   19                                                            
CONECT   25    1   17                                                       
CONECT   26    2   18                                                       
CONECT   27    3   19                                                       
CONECT   28   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
(7'R,8's)-methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-Oic acid	Generator

Chemical Formula

C₂₁H₂₂O₇

Average Mass

386.4000 Da

Monoisotopic Mass

386.13655 Da

IUPAC Name

methyl (2Z)-3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate

Traditional Name

methyl (2Z)-3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C/C1=CC2=C(OC(C2CO)C2=CC(OC)=C(O)C=C2)C(OC)=C1

InChI Identifier

InChI=1/C21H22O7/c1-25-17-10-13(5-6-16(17)23)20-15(11-22)14-8-12(4-7-19(24)27-3)9-18(26-2)21(14)28-20/h4-10,15,20,22-23H,11H2,1-3H3/b7-4-

InChI Key

DPDJZJNYBSGDHT-DAXSKMNVNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Neolignan skeleton
Coumaric acid or derivatives
Methoxyphenol
Coumaran
Benzofuran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Ether
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organooxygen compound
Primary alcohol
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	2.53	ChemAxon
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	103.09 m³·mol⁻¹	ChemAxon
Polarizability	40.07 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

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

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate (NP0335784)

MOL for NP0335784 ((7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

3D MOL for NP0335784 ((7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

3D SDF for NP0335784 ((7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

3D-SDF for NP0335784 ((7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

PDB for NP0335784 ((7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

3D PDB for NP0335784 ((7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

SMILES for NP0335784 ((7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

INCHI for NP0335784 ((7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

Structure for NP0335784 ((7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

3D Structure for NP0335784 ((7'R*,8'S*)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

Showing NP-Card for (7'R,8'S)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate (NP0335784)

MOL for NP0335784 ((7'R,8'S)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

3D MOL for NP0335784 ((7'R,8'S)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

3D SDF for NP0335784 ((7'R,8'S)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

3D-SDF for NP0335784 ((7'R,8'S)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

PDB for NP0335784 ((7'R,8'S)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

3D PDB for NP0335784 ((7'R,8'S)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

SMILES for NP0335784 ((7'R,8'S)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

INCHI for NP0335784 ((7'R,8'S)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

Structure for NP0335784 ((7'R,8'S)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)

3D Structure for NP0335784 ((7'R,8'S)-Methyl 4,7'-epoxy-3,8'-bilign-7-ene-4',9'-dihydroxy-3',5-dimethoxy-9-oate)