NP-MRD: Showing NP-Card for (r)-demethylvestitol (NP0247412)

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Record Information

Version

2.0

Created at

2022-09-07 09:15:40 UTC

Updated at

2022-09-07 09:15:41 UTC

NP-MRD ID

NP0247412

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(r)-demethylvestitol

Description

UNII-A573928L5Y belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton. (r)-demethylvestitol is found in Cadophora gregata, Caragana tibetica, Erythrina sandwicensis, Lotus angustissimus, Lotus uliginosus, Phaseolus coccineus and Phaseolus vulgaris. Based on a literature review very few articles have been published on UNII-A573928L5Y.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.9603   -0.0349    0.3822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5538    0.0374    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8079   -0.1655    1.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4201   -0.0889    1.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7156    0.1966    0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2708    0.1703    0.3748 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3339    0.4907    1.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381   -0.2560    1.8420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553   -0.2647    0.6958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6278   -0.8113    0.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4913   -0.8656   -0.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7392   -1.4294   -0.0592 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0787   -0.3564   -1.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8054    0.1807   -1.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9406    0.2413   -0.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5426    0.8420   -0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678    0.3981   -0.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8353    0.6890   -2.0066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8565    0.3181   -0.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4416   -0.9343    0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3412   -0.3949    2.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9539   -0.2891    2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0128   -0.9656    0.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6624    1.5909    1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2947    0.4038    2.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133   -1.2029    1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4540   -1.5362   -0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7549   -0.4008   -2.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4820    0.5834   -2.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066    0.5985   -1.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6909    1.9221   -0.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4037    0.8489   -2.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4068    0.4848   -1.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  5 17  1  0
 17 18  1  0
 17 19  2  0
 19  2  1  0
 16  6  1  0
 15  9  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  6
  7 24  1  0
  7 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
M  END


  Mrv1652309072211152D          

 19 21  0  0  1  0            999 V2000
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  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
   -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  2  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
    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
    2.8579    0.0000    0.0000 C   0  0  0  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
    4.2868   -0.0000    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  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
    0.0000   -2.4750    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
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247412

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C([C@@H]2COC3=CC(O)=CC=C3C2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c16-11-3-4-13(14(18)6-11)10-5-9-1-2-12(17)7-15(9)19-8-10/h1-4,6-7,10,16-18H,5,8H2/t10-/m0/s1

> <INCHI_KEY>
CJZBXHPHEBCWLV-JTQLQIEISA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.273

> <EXACT_MASS>
258.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.688835299604577

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(3R)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]benzene-1,3-diol

> <JCHEM_LOGP>
2.888112555666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.93781658059375

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.328246630474638

> <JCHEM_PKA_STRONGEST_BASIC>
-4.855579298157446

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
70.9411

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(3R)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15    6                                                       
CONECT   17    5   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    2                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₄

Average Mass

258.2730 Da

Monoisotopic Mass

258.08921 Da

IUPAC Name

4-[(3R)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]benzene-1,3-diol

Traditional Name

4-[(3R)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

OC1=CC=C([C@@H]2COC3=CC(O)=CC=C3C2)C(O)=C1

InChI Identifier

InChI=1S/C15H14O4/c16-11-3-4-13(14(18)6-11)10-5-9-1-2-12(17)7-15(9)19-8-10/h1-4,6-7,10,16-18H,5,8H2/t10-/m0/s1

InChI Key

CJZBXHPHEBCWLV-JTQLQIEISA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Cadophora gregata	LOTUS Database	35616633
Caragana tibetica	LOTUS Database	35616633
Erythrina sandwicensis	LOTUS Database	35616633
Lotus angustissimus	LOTUS Database	35616633
Lotus uliginosus	LOTUS Database	35616633
Phaseolus coccineus	LOTUS Database	35616633
Phaseolus vulgaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanols

Alternative Parents

Substituents

Isoflavanol
Hydroxyisoflavonoid
Chromane
Benzopyran
1-benzopyran
Resorcinol
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organooxygen compound
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	2.89	ChemAxon
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.94 m³·mol⁻¹	ChemAxon
Polarizability	26.69 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

Not Available

Chemspider ID

33823851

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92021067

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (r)-demethylvestitol (NP0247412)

MOL for NP0247412 ((r)-demethylvestitol)

3D MOL for NP0247412 ((r)-demethylvestitol)

3D SDF for NP0247412 ((r)-demethylvestitol)

3D-SDF for NP0247412 ((r)-demethylvestitol)

PDB for NP0247412 ((r)-demethylvestitol)

3D PDB for NP0247412 ((r)-demethylvestitol)

SMILES for NP0247412 ((r)-demethylvestitol)

INCHI for NP0247412 ((r)-demethylvestitol)

Structure for NP0247412 ((r)-demethylvestitol)

3D Structure for NP0247412 ((r)-demethylvestitol)