NP-MRD: Showing NP-Card for Demethylvestitol (NP0047807)

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Record Information

Version

2.0

Created at

2022-03-17 20:46:18 UTC

Updated at

2022-03-17 20:46:18 UTC

NP-MRD ID

NP0047807

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Demethylvestitol

Description

Demethylvestitol, also known as arduan or pipecurium bromide, belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton. Thus, demethylvestitol is considered to be a flavonoid lipid molecule. Demethylvestitol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Demethylvestitol has been detected, but not quantified in, several different foods, such as common beans, green beans, pulses, scarlet beans, and yellow wax beans. Demethylvestitol is found in Anthyllis vulneraria , Caragana tibetica, Endosamara racemosa, Erythrina sandwicensis, Hosackia americana, Lotus edulis, Lotus spp., Lotus uliginosus, Tetragonolobus spp., Vigna angularis and Vigna mungo. This could make demethylvestitol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061307292D          

 19 21  0  0  0  0            999 V2000
    1.4289    0.0000    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    5.7158    0.0000    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
    3.5724   -1.2375    0.0000 C   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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  2  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 11  6  2  0  0  0  0
 12  2  1  0  0  0  0
 12  7  2  0  0  0  0
 13  4  1  0  0  0  0
 13 10  1  0  0  0  0
 14  6  1  0  0  0  0
 14 13  2  0  0  0  0
 15  7  1  0  0  0  0
 15  9  2  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 14  1  0  0  0  0
 19  8  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047807

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2

> <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

> <INCHI_KEY>
CJZBXHPHEBCWLV-UHFFFAOYSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.2693

> <EXACT_MASS>
258.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.15727209159045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.888112555666666

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.937816580595957

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.328246630474686

> <JCHEM_PKA_STRONGEST_BASIC>
-4.855579298160206

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
70.94110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
demethylvestitol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   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  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1   12                                                       
CONECT    3    4   11                                                       
CONECT    4    3   13                                                       
CONECT    5    9   10                                                       
CONECT    6   11   14                                                       
CONECT    7   12   15                                                       
CONECT    8   10   19                                                       
CONECT    9    1    5   15                                                  
CONECT   10    5    8   13                                                  
CONECT   11    3    6   16                                                  
CONECT   12    2    7   17                                                  
CONECT   13    4   10   14                                                  
CONECT   14    6   13   18                                                  
CONECT   15    7    9   19                                                  
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   14                                                            
CONECT   19    8   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
3,4-Dihydro-3-(2,4-dihydroxyphenyl)-7-hydroxy-2H-1-benzopyran	HMDB
4-(3,4-Dihydro-7-hydroxy-2H-1-benzopyran-4-yl)-1,3-benzenediol, 9ci	HMDB
7,2',4'-Trihydroxyisoflavan	HMDB
Arduan	HMDB
Pipecurium bromide	HMDB
Pipecuronio bromuro	HMDB
Pipecuronium	HMDB
Pipecuronium bromide	HMDB
Pipecuronium, dibromide	HMDB

Chemical Formula

C₁₅H₁₄O₄

Average Mass

258.2693 Da

Monoisotopic Mass

258.08921 Da

IUPAC Name

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

Traditional Name

demethylvestitol

CAS Registry Number

65332-45-8

SMILES

OC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2

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

InChI Key

CJZBXHPHEBCWLV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anthyllis vulneraria	Plant	KNApSAcK
Caragana tibetica	LOTUS Database	35616633
Endosamara racemosa	LOTUS Database	35616633
Erythrina sandwicensis	Plant	KNApSAcK
Hosackia americana	-	KNApSAcK
Lotus edulis	LOTUS Database	35616633
Lotus spp.	Plant	KNApSAcK
Lotus uliginosus	Plant	KNApSAcK
Phaseolus coccineus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tetragonolobus spp.	-	KNApSAcK
Vigna angularis	LOTUS Database	35616633
Vigna mungo	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

Isoflavans (LMPK12080027 )

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	2.16	ALOGPS
logP	2.89	ChemAxon
logS	-3.5	ALOGPS
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	27.16 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

HMDB0033986

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012218

KNApSAcK ID

C00009708

Chemspider ID

509323

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

585939

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Demethylvestitol (NP0047807)

MOL for NP0047807 (Demethylvestitol)

3D MOL for NP0047807 (Demethylvestitol)

3D SDF for NP0047807 (Demethylvestitol)

3D-SDF for NP0047807 (Demethylvestitol)

PDB for NP0047807 (Demethylvestitol)

3D PDB for NP0047807 (Demethylvestitol)

SMILES for NP0047807 (Demethylvestitol)

INCHI for NP0047807 (Demethylvestitol)

Structure for NP0047807 (Demethylvestitol)

3D Structure for NP0047807 (Demethylvestitol)