NP-MRD: Showing NP-Card for 2'-O-Methylvestitol (NP0082256)

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Record Information

Version

2.0

Created at

2022-04-29 03:17:59 UTC

Updated at

2022-04-29 03:17:59 UTC

NP-MRD ID

NP0082256

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'-O-Methylvestitol

Description

(-)-Sativan, also known as sativin, 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. Thus, (-)-sativan is considered to be a flavonoid (-)-sativan is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 2'-O-Methylvestitol is found in Baphia nitida, Caragana tibetica, Centrolobium tomentosum, Gliricidia sepium , Lotus corniculatus, Medicago sativa, Medicago spp., Trifolium spp., Trigonella spp. and Wisteria brachybotrys. 2'-O-Methylvestitol was first documented in 2020 (PMID: 32231566). Based on a literature review very few articles have been published on (-)-sativan.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -5.5117    1.6556    2.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4133    0.9235    2.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2302    0.8232    2.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1115    1.4202    0.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427    1.3209    0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8440    0.6260    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4314    0.4763   -0.1935 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4366    1.2951   -1.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542    1.3268   -1.9644 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4938    0.1584   -1.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7299    0.1598   -2.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5099   -0.9529   -2.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356   -0.9128   -3.2511 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407   -2.0881   -1.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8097   -2.0912   -1.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0172   -0.9674   -1.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6807   -0.9578   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9640    0.0248    1.7847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -0.6823    2.2707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0035   -1.2917    3.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1382    0.1277    2.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3739    1.6581    2.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1600    2.7229    2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7246    1.3422    1.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9574    1.9780    0.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8657    1.8001   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3161    0.8017    0.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2357    0.7757   -2.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0691    2.3089   -1.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0790    1.0730   -3.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8288   -1.1541   -4.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6793   -2.9565   -1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732   -2.9991   -0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7165   -1.6554    0.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -1.2337   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9618   -1.7246    3.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3816   -0.6142    4.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7093   -2.1719    3.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2267   -0.3453    3.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 21  2  0
 21 18  1  0
 18 19  1  0
 19 20  1  0
 18  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  4  3  1  0
 17  7  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 21 39  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
  5 26  1  0
  4 25  1  0
  7 27  1  1
  8 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
M  END


  Mrv1652304292205182D          

 21 23  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  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
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0082256

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C(C=C1)[C@@H]1COC2=CC(O)=CC=C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O4/c1-19-14-5-6-15(17(9-14)20-2)12-7-11-3-4-13(18)8-16(11)21-10-12/h3-6,8-9,12,18H,7,10H2,1-2H3/t12-/m0/s1

> <INCHI_KEY>
TUXCLJQCYVCGDW-LBPRGKRZSA-N

> <FORMULA>
C17H18O4

> <MOLECULAR_WEIGHT>
286.327

> <EXACT_MASS>
286.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
30.87353547342507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-3-(2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
3.179900667666667

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.781761268370131

> <JCHEM_PKA_STRONGEST_BASIC>
-4.365104800018318

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
79.90570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-sativan

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   21                                                  
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   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14   18                                                       
CONECT   18   17                                                            
CONECT   19   12   20                                                       
CONECT   20   19                                                            
CONECT   21    1                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
(3R)-3-(2,4-Dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol	ChEBI
2-Hydroxy-2',4'-dimethoxyisoflavan	ChEBI
Sativin	ChEBI

Chemical Formula

C₁₇H₁₈O₄

Average Mass

286.3270 Da

Monoisotopic Mass

286.12051 Da

IUPAC Name

(3R)-3-(2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

(-)-sativan

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C(C=C1)[C@@H]1COC2=CC(O)=CC=C2C1

InChI Identifier

InChI=1S/C17H18O4/c1-19-14-5-6-15(17(9-14)20-2)12-7-11-3-4-13(18)8-16(11)21-10-12/h3-6,8-9,12,18H,7,10H2,1-2H3/t12-/m0/s1

InChI Key

TUXCLJQCYVCGDW-LBPRGKRZSA-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
Baphia nitida	LOTUS Database	35616633
Caragana tibetica	LOTUS Database	35616633
Centrolobium tomentosum	LOTUS Database	35616633
Gliricidia sepium	Plant	KNApSAcK
Lotus corniculatus	LOTUS Database	35616633
Medicago sativa	LOTUS Database	35616633
Medicago spp.	Plant	KNApSAcK
Trifolium spp.	Plant	KNApSAcK
Trigonella spp.	Plant	KNApSAcK
Wisteria brachybotrys	LOTUS Database	35616633

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

2p-methoxyisoflavonoid-skeleton
4p-methoxyisoflavonoid
Hydroxyisoflavonoid
Isoflavanol
Isoflavan
Chromane
Benzopyran
M-dimethoxybenzene
Dimethoxybenzene
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyisoflavan (CHEBI:115 )
hydroxyisoflavans (CHEBI:115 )
isoflavans (C10526 )
Isoflavanes (C10526 )
Isoflavans (LMPK12080025 )

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	3.13	ALOGPS
logP	3.18	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.91 m³·mol⁻¹	ChemAxon
Polarizability	30.87 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002570

Chemspider ID

149123

KEGG Compound ID

C10526

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

170570

PDB ID

Not Available

ChEBI ID

115

Good Scents ID

Not Available

References

General References

Peng F, Xiong L, Peng C: (-)-Sativan Inhibits Tumor Development and Regulates miR-200c/PD-L1 in Triple Negative Breast Cancer Cells. Front Pharmacol. 2020 Mar 13;11:251. doi: 10.3389/fphar.2020.00251. eCollection 2020. [PubMed:32231566 ]

Showing NP-Card for 2'-O-Methylvestitol (NP0082256)

MOL for NP0082256 (2'-O-Methylvestitol)

3D MOL for NP0082256 (2'-O-Methylvestitol)

3D SDF for NP0082256 (2'-O-Methylvestitol)

3D-SDF for NP0082256 (2'-O-Methylvestitol)

PDB for NP0082256 (2'-O-Methylvestitol)

3D PDB for NP0082256 (2'-O-Methylvestitol)

SMILES for NP0082256 (2'-O-Methylvestitol)

INCHI for NP0082256 (2'-O-Methylvestitol)

Structure for NP0082256 (2'-O-Methylvestitol)

3D Structure for NP0082256 (2'-O-Methylvestitol)