NP-MRD: Showing NP-Card for (+)-Vestitol (NP0051494)

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Record Information

Version

2.0

Created at

2022-04-27 22:50:21 UTC

Updated at

2022-04-27 22:50:21 UTC

NP-MRD ID

NP0051494

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Vestitol

Description

(+)-Vestitol 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, (+)-vestitol is considered to be a flavonoid (+)-vestitol 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. (+)-Vestitol is found in Centrolobium tomentosum, Dalbergia candenatensis, Dalbergia parviflora, Dalbergia sissoo, Dalbergia variabilis, Gliricidia sepium, Glycyrrhiza spp., Glycyrrhiza uralensis, Hedysarum theinum, Machaerium vestitum, Wisteria brachybotrys and Zollernia paraensis. (+)-Vestitol was first documented in 2020 (PMID: 33352963). Based on a literature review very few articles have been published on (+)-vestitol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -6.1438    0.2130   -0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1288    0.8049    0.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8088    0.4544    0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8911    1.0977    1.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563    0.7887    1.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0498   -0.1798    0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3895   -0.2426    0.3532 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0516   -0.4052    1.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -0.9976    1.4768 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060   -0.3973    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4031    0.0403    0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0296    0.6340   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3283    1.0399   -0.4455 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3645    0.7988   -1.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0572    0.3479   -1.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4332   -0.2386   -0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0651   -0.8139   -0.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9808   -0.7903   -0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5344   -1.7713   -1.2064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3383   -0.4944   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9650    0.9292   -0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7852   -0.1848   -0.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5798   -0.6125    0.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2244    1.8601    2.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834    1.3428    2.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6093    0.9385    0.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2212    0.5594    2.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828   -1.0877    2.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9331   -0.0935    1.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0544    0.3842   -0.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8348    1.2843   -2.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621    0.4841   -2.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5137   -0.4808   -1.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2232   -1.9097   -0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1809   -2.2710   -1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0062   -1.0309   -0.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 20  2  0
 20 18  1  0
 18 19  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 21  1  0
  1 22  1  0
  1 23  1  0
 20 36  1  0
 19 35  1  0
  5 25  1  0
  4 24  1  0
  7 26  1  6
  8 27  1  0
  8 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 17 34  1  0
M  END


  Mrv1652304282200502D          

 20 22  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  1  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
   -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  6  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
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051494

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O4/c1-19-13-4-5-14(15(18)8-13)11-6-10-2-3-12(17)7-16(10)20-9-11/h2-5,7-8,11,17-18H,6,9H2,1H3/t11-/m1/s1

> <INCHI_KEY>
XRVFNNUXNVWYTI-LLVKDONJSA-N

> <FORMULA>
C16H16O4

> <MOLECULAR_WEIGHT>
272.3

> <EXACT_MASS>
272.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.306835970391962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
3.0340066116666664

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.087859766927583

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.480129139253403

> <JCHEM_PKA_STRONGEST_BASIC>
-4.541703356647494

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
75.42340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vestitol

> <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      -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  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
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                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
(3S)-Vestitol	ChEBI

Chemical Formula

C₁₆H₁₆O₄

Average Mass

272.3000 Da

Monoisotopic Mass

272.10486 Da

IUPAC Name

(3S)-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

vestitol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H16O4/c1-19-13-4-5-14(15(18)8-13)11-6-10-2-3-12(17)7-16(10)20-9-11/h2-5,7-8,11,17-18H,6,9H2,1H3/t11-/m1/s1

InChI Key

XRVFNNUXNVWYTI-LLVKDONJSA-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
Centrolobium tomentosum	LOTUS Database	35616633
Dalbergia candenatensis	LOTUS Database	35616633
Dalbergia parviflora	LOTUS Database	35616633
Dalbergia sissoo	LOTUS Database	35616633
Dalbergia variabilis	Plant	KNApSAcK
Gliricidia sepium	LOTUS Database	35616633
Glycyrrhiza spp.	Plant	KNApSAcK
Glycyrrhiza uralensis	LOTUS Database	35616633
Hedysarum theinum	LOTUS Database	35616633
Machaerium vestitum	Plant	KNApSAcK
Wisteria brachybotrys	LOTUS Database	35616633
Zollernia paraensis	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
Isoflavanol
Hydroxyisoflavonoid
Isoflavan
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

vestitol (CHEBI:9971 )
isoflavans (C10540 )
Isoflavanes (C10540 )
Isoflavans (LMPK12080026 )

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	2.89	ALOGPS
logP	3.03	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.48	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.42 m³·mol⁻¹	ChemAxon
Polarizability	29.31 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

C00002583

Chemspider ID

154266

KEGG Compound ID

C10540

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

177149

PDB ID

Not Available

ChEBI ID

9971

Good Scents ID

Not Available

References

General References

Muhammad I, Jacob MR, Ibrahim MA, Raman V, Kumarihamy M, Wang M, Al-Adhami T, Hind C, Clifford M, Martin B, Zhao J, Sutton JM, Rahman KM: Antimicrobial Constituents from Machaerium Pers.: Inhibitory Activities and Synergism of Machaeriols and Machaeridiols against Methicillin-Resistant Staphylococcus aureus, Vancomycin-Resistant Enterococcus faecium, and Permeabilized Gram-Negative Pathogens. Molecules. 2020 Dec 18;25(24). pii: molecules25246000. doi: 10.3390/molecules25246000. [PubMed:33352963 ]

Showing NP-Card for (+)-Vestitol (NP0051494)

MOL for NP0051494 ((+)-Vestitol)

3D MOL for NP0051494 ((+)-Vestitol)

3D SDF for NP0051494 ((+)-Vestitol)

3D-SDF for NP0051494 ((+)-Vestitol)

PDB for NP0051494 ((+)-Vestitol)

3D PDB for NP0051494 ((+)-Vestitol)

SMILES for NP0051494 ((+)-Vestitol)

INCHI for NP0051494 ((+)-Vestitol)

Structure for NP0051494 ((+)-Vestitol)

3D Structure for NP0051494 ((+)-Vestitol)