NP-MRD: Showing NP-Card for Vestitol-(5'->3)-7,2'-dihydroxy-4'-methoxyflav-2-ene (NP0054416)

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Record Information

Version

2.0

Created at

2022-04-28 00:46:53 UTC

Updated at

2022-04-28 00:46:53 UTC

NP-MRD ID

NP0054416

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vestitol-(5'->3)-7,2'-dihydroxy-4'-methoxyflav-2-ene

Description

2-(2-Hydroxy-4-methoxyphenyl)-3-{4-hydroxy-5-[(3S)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]-2-methoxyphenyl}-4H-chromen-7-ol belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Vestitol-(5'->3)-7,2'-dihydroxy-4'-methoxyflav-2-ene is found in Dalbergia odorifera . Based on a literature review very few articles have been published on 2-(2-hydroxy-4-methoxyphenyl)-3-{4-hydroxy-5-[(3S)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]-2-methoxyphenyl}-4H-chromen-7-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202462D          

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M  END

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  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  0  0  0  0
 21 27  1  0  0  0  0
 17 27  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 31 35  1  0  0  0  0
 35 36  1  0  0  0  0
 14 37  1  0  0  0  0
 37 38  1  0  0  0  0
 12 39  1  0  0  0  0
  1 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054416

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C(O)=C1)C1=C(CC2=C(O1)C=C(O)C=C2)C1=CC([C@H]2COC3=CC(O)=CC=C3C2)=C(O)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C32H28O8/c1-37-22-7-8-23(27(35)13-22)32-26(10-18-4-6-21(34)12-30(18)40-32)25-14-24(28(36)15-31(25)38-2)19-9-17-3-5-20(33)11-29(17)39-16-19/h3-8,11-15,19,33-36H,9-10,16H2,1-2H3/t19-/m1/s1

> <INCHI_KEY>
YXFWBLAAIYJYOB-LJQANCHMSA-N

> <FORMULA>
C32H28O8

> <MOLECULAR_WEIGHT>
540.568

> <EXACT_MASS>
540.178417862

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
57.55524278485664

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2-hydroxy-4-methoxyphenyl)-3-{4-hydroxy-5-[(3S)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]-2-methoxyphenyl}-4H-chromen-7-ol

> <ALOGPS_LOGP>
5.27

> <JCHEM_LOGP>
5.563872770333333

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.157398261035063

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.489492337120101

> <JCHEM_PKA_STRONGEST_BASIC>
-4.328642359602563

> <JCHEM_POLAR_SURFACE_AREA>
117.84000000000002

> <JCHEM_REFRACTIVITY>
150.37540000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-hydroxy-4-methoxyphenyl)-3-{4-hydroxy-5-[(3S)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]-2-methoxyphenyl}-4H-chromen-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0     -13.337  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   40                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12   16                                                  
CONECT   12   11   13   39                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   37                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15   18   27                                                  
CONECT   18   17   19   28                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24                                                            
CONECT   27   21   17                                                       
CONECT   28   18   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   35                                                  
CONECT   32   31   33                                                       
CONECT   33   32   28   34                                                  
CONECT   34   33                                                            
CONECT   35   31   36                                                       
CONECT   36   35                                                            
CONECT   37   14   38                                                       
CONECT   38   37                                                            
CONECT   39   12                                                            
CONECT   40    1                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₈O₈

Average Mass

540.5680 Da

Monoisotopic Mass

540.17842 Da

IUPAC Name

2-(2-hydroxy-4-methoxyphenyl)-3-{4-hydroxy-5-[(3S)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]-2-methoxyphenyl}-4H-chromen-7-ol

Traditional Name

2-(2-hydroxy-4-methoxyphenyl)-3-{4-hydroxy-5-[(3S)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]-2-methoxyphenyl}-4H-chromen-7-ol

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C(O)=C1)C1=C(CC2=C(O1)C=C(O)C=C2)C1=CC([C@H]2COC3=CC(O)=CC=C3C2)=C(O)C=C1OC

InChI Identifier

InChI=1S/C32H28O8/c1-37-22-7-8-23(27(35)13-22)32-26(10-18-4-6-21(34)12-30(18)40-32)25-14-24(28(36)15-31(25)38-2)19-9-17-3-5-20(33)11-29(17)39-16-19/h3-8,11-15,19,33-36H,9-10,16H2,1-2H3/t19-/m1/s1

InChI Key

YXFWBLAAIYJYOB-LJQANCHMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dalbergia odorifera	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

4'-O-methylated isoflavonoids

Alternative Parents

Substituents

4p-methoxyisoflavonoid
4p-methoxyflavonoid-skeleton
2p-methoxyisoflavonoid-skeleton
Hydroxyisoflavonoid
Neolignan skeleton
Isoflavanol
Hydroxyflavonoid
7-hydroxyflavonoid
Isoflavan
Isoflav-2-ene skeleton
Stilbene
1-benzopyran
Methoxyphenol
Benzopyran
Chromane
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen 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	5.27	ALOGPS
logP	5.56	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	117.84 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	150.38 m³·mol⁻¹	ChemAxon
Polarizability	57.56 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

163054202

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Vestitol-(5'->3)-7,2'-dihydroxy-4'-methoxyflav-2-ene (NP0054416)

MOL for NP0054416 (Vestitol-(5'->3)-7,2'-dihydroxy-4'-methoxyflav-2-ene)

3D MOL for NP0054416 (Vestitol-(5'->3)-7,2'-dihydroxy-4'-methoxyflav-2-ene)

3D SDF for NP0054416 (Vestitol-(5'->3)-7,2'-dihydroxy-4'-methoxyflav-2-ene)

3D-SDF for NP0054416 (Vestitol-(5'->3)-7,2'-dihydroxy-4'-methoxyflav-2-ene)

PDB for NP0054416 (Vestitol-(5'->3)-7,2'-dihydroxy-4'-methoxyflav-2-ene)

3D PDB for NP0054416 (Vestitol-(5'->3)-7,2'-dihydroxy-4'-methoxyflav-2-ene)

SMILES for NP0054416 (Vestitol-(5'->3)-7,2'-dihydroxy-4'-methoxyflav-2-ene)

INCHI for NP0054416 (Vestitol-(5'->3)-7,2'-dihydroxy-4'-methoxyflav-2-ene)

Structure for NP0054416 (Vestitol-(5'->3)-7,2'-dihydroxy-4'-methoxyflav-2-ene)

3D Structure for NP0054416 (Vestitol-(5'->3)-7,2'-dihydroxy-4'-methoxyflav-2-ene)