NP-MRD: Showing NP-Card for (-)-3-Hydroxy-9-methoxypterocarpan (NP0047766)

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Record Information

Version

2.0

Created at

2022-03-17 20:45:37 UTC

Updated at

2022-03-17 20:45:37 UTC

NP-MRD ID

NP0047766

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-3-Hydroxy-9-methoxypterocarpan

Description

(-)-3-Hydroxy-9-methoxypterocarpan belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids (-)-3-Hydroxy-9-methoxypterocarpan is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (-)-3-Hydroxy-9-methoxypterocarpan has been detected, but not quantified in, alfalfa and cowpea. (-)-3-Hydroxy-9-methoxypterocarpan is found in Butea monosperma, Caragana tibetica, Caragana tibetica KOM., Centrolobium sclerophyllum, Dalbergia decipularis, Dalbergia frutescens, Dalbergia monetaria , Dalbergia nitidula , Dalbergia odorifera, Dalbergia sissoo, Dalbergia volubilis , Dalea versicolor, Delea versicolor, Gliricidia sepium, Glycyrrhiza uralensis, Hedysarum polybotrys, Hedysarum theinum, Lonchocarpus negrensis, Maackia amurensis, Machaerium acutifolium, Machaerium aristulatum, Machaerium kuhlmannii, Machaerium nyctitans, Machaerium vestitum, Melilotus messanensis, Millettia leucantha, Ononis vaginalis, Ononis viscosa, Platymiscium floribundum, Psorothamnus spinosus, Sophora flavescens, Sophora japonica L. , Sophora secundiflora, Taverniera abyssinica, Tephrosia purpurea and Zollernia paraensis. This could make (-)-3-hydroxy-9-methoxypterocarpan a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310051704172D          

 20 23  0  0  0  0            999 V2000
   -0.9390   -2.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -2.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980   -1.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156   -2.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -2.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450   -2.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453   -0.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -2.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  9  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 12  4  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 14 12  2  0  0  0  0
 15  7  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17  9  1  0  0  0  0
 18  1  1  0  0  0  0
 18 10  1  0  0  0  0
 19  8  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047766

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c1-18-10-3-5-11-13-8-19-14-6-9(17)2-4-12(14)16(13)20-15(11)7-10/h2-7,13,16-17H,8H2,1H3

> <INCHI_KEY>
NSRJSISNDPOJOP-UHFFFAOYSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.28

> <EXACT_MASS>
270.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.925537743960632

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaen-5-ol

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
2.509223396333333

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.420754148461814

> <JCHEM_PKA_STRONGEST_BASIC>
-4.392070210867522

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
73.06110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaen-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0      -1.753  -4.262   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.899  -4.971   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.985  -2.851   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.362  -5.059   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.353  -2.145   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.827  -1.196   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.592  -3.595   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.911  -4.389   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.649  -2.977   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.517  -3.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.135  -2.572   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.210  -2.396   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.576  -4.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.980  -3.859   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.129  -3.507   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.365  -1.108   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.016  -5.061   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    4    9                                                       
CONECT    3    5   10                                                       
CONECT    4    2   12                                                       
CONECT    5    3   11                                                       
CONECT    6    9   14                                                       
CONECT    7   10   15                                                       
CONECT    8   13   19                                                       
CONECT    9    2    6   17                                                  
CONECT   10    3    7   18                                                  
CONECT   11    5   13   15                                                  
CONECT   12    4   14   16                                                  
CONECT   13    8   11   16                                                  
CONECT   14    6   12   19                                                  
CONECT   15    7   11   20                                                  
CONECT   16   12   13   20                                                  
CONECT   17    9                                                            
CONECT   18    1   10                                                       
CONECT   19    8   14                                                       
CONECT   20   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₄

Average Mass

270.2800 Da

Monoisotopic Mass

270.08921 Da

IUPAC Name

14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaen-5-ol

Traditional Name

14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaen-5-ol

CAS Registry Number

32383-76-9

SMILES

COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2

InChI Identifier

InChI=1S/C16H14O4/c1-18-10-3-5-11-13-8-19-14-6-9(17)2-4-12(14)16(13)20-15(11)7-10/h2-7,13,16-17H,8H2,1H3

InChI Key

NSRJSISNDPOJOP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Butea monosperma	LOTUS Database	35616633
Caragana tibetica	LOTUS Database	35616633
Caragana tibetica KOM.	Plant	KNApSAcK
Centrolobium sclerophyllum	LOTUS Database	35616633
Dalbergia decipularis	Plant	KNApSAcK
Dalbergia frutescens	Plant	KNApSAcK
Dalbergia monetaria	Plant	KNApSAcK
Dalbergia nitidula	Plant	KNApSAcK
Dalbergia odorifera	LOTUS Database	35616633
Dalbergia sissoo	LOTUS Database	35616633
Dalbergia volubilis	Plant	KNApSAcK
Dalea versicolor	Plant	KNApSAcK
Delea versicolor	-	KNApSAcK
Gliricidia sepium	LOTUS Database	35616633
Glycyrrhiza uralensis	LOTUS Database	35616633
Hedysarum polybotrys	LOTUS Database	35616633
Hedysarum theinum	LOTUS Database	35616633
Lonchocarpus negrensis	Plant	KNApSAcK
Maackia amurensis	LOTUS Database	35616633
Machaerium acutifolium	Plant	KNApSAcK
Machaerium aristulatum	Plant	KNApSAcK
Machaerium kuhlmannii	Plant	KNApSAcK
Machaerium nictitans	Plant	KNApSAcK
Machaerium vestitum	Plant	KNApSAcK
Medicago sativa	FooDB	KNAPSACK
Melilotus messanensis	LOTUS Database	35616633
Millettia leucantha	LOTUS Database	35616633
Ononis vaginalis	LOTUS Database	35616633
Ononis viscosa	LOTUS Database	35616633
Platymiscium floribundum	LOTUS Database	35616633
Psorothamnus spinosus	LOTUS Database	35616633
Sophora flavescens	LOTUS Database	35616633
Sophora japonica L.	Plant	KNApSAcK
Sophora secundiflora	LOTUS Database	35616633
Taverniera abyssinica	LOTUS Database	35616633
Tephrosia purpurea	LOTUS Database	35616633
Vigna unguiculata	FooDB	KNAPSACK
Zollernia paraensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Isoflavan
Chromane
1-benzopyran
Benzopyran
Coumaran
Benzofuran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pterocarpans (CHEBI:16114 )
a small molecule (CPD-3402 )

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	3.07	ALOGPS
logP	2.51	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.42	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	1	ChemAxon
Refractivity	73.06 m³·mol⁻¹	ChemAxon
Polarizability	27.93 Å³	ChemAxon
Number of Rings	4	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

HMDB0146681

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012035

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

Not Available

PDB ID

Not Available

ChEBI ID

16114

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-3-Hydroxy-9-methoxypterocarpan (NP0047766)

MOL for NP0047766 ((-)-3-Hydroxy-9-methoxypterocarpan)

3D MOL for NP0047766 ((-)-3-Hydroxy-9-methoxypterocarpan)

3D SDF for NP0047766 ((-)-3-Hydroxy-9-methoxypterocarpan)

3D-SDF for NP0047766 ((-)-3-Hydroxy-9-methoxypterocarpan)

PDB for NP0047766 ((-)-3-Hydroxy-9-methoxypterocarpan)

3D PDB for NP0047766 ((-)-3-Hydroxy-9-methoxypterocarpan)

SMILES for NP0047766 ((-)-3-Hydroxy-9-methoxypterocarpan)

INCHI for NP0047766 ((-)-3-Hydroxy-9-methoxypterocarpan)

Structure for NP0047766 ((-)-3-Hydroxy-9-methoxypterocarpan)

3D Structure for NP0047766 ((-)-3-Hydroxy-9-methoxypterocarpan)