NP-MRD: Showing NP-Card for 3,4,9-Trihydroxypterocarpan (NP0047813)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 20:46:24 UTC

Updated at

2022-03-17 20:46:24 UTC

NP-MRD ID

NP0047813

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,9-Trihydroxypterocarpan

Description

3,4,9-Trihydroxypterocarpan, also known as 4-hydroxydemethylmedicarpin, 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. Thus, 3,4,9-trihydroxypterocarpan is considered to be a flavonoid lipid molecule. 3,4,9-Trihydroxypterocarpan is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3,4,9-trihydroxypterocarpan has been detected, but not quantified in, a few different foods, such as alfalfa, herbs and spices, and pulses. 3,4,9-Trihydroxypterocarpan is found in Melilotus alba. This could make 3,4,9-trihydroxypterocarpan a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307292D          

 20 23  0  0  0  0            999 V2000
    5.7521    1.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188    0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    2.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763    2.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0972    2.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913    2.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248    1.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    1.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289    1.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053    1.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640    2.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579    0.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0762    1.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816    0.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5246    2.4062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2184    1.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6869    0.1762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    0.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5923    2.3879    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
  7  1  1  0  0  0  0
  7  5  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 12  8  2  0  0  0  0
 13 11  2  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16  7  1  0  0  0  0
 17 11  1  0  0  0  0
 18 13  1  0  0  0  0
 19  6  1  0  0  0  0
 19 15  1  0  0  0  0
 20 12  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047813

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-7-1-2-8-10-6-19-15-9(3-4-11(17)13(15)18)14(10)20-12(8)5-7/h1-5,10,14,16-18H,6H2

> <INCHI_KEY>
CLHTZHIBHTWFEM-UHFFFAOYSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.2528

> <EXACT_MASS>
272.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.026628268653816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,6,14-triol

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
2.059764018666666

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.811778317015424

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.205380611419981

> <JCHEM_PKA_STRONGEST_BASIC>
-4.620187150767641

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
70.5597

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,6,14-triol

> <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      10.737   2.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.368   1.542   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.360   4.456   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.822   4.367   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.515   4.618   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.895   0.593   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.810   3.786   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.073   2.374   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.205   3.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.587   1.969   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.130   2.992   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.146   3.913   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.975   1.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.742   3.256   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.512   1.793   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.179   4.492   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.408   2.904   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.282   0.329   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.357   0.505   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.706   4.457   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    8                                                       
CONECT    3    4    9                                                       
CONECT    4    3   11                                                       
CONECT    5    7   12                                                       
CONECT    6   10   19                                                       
CONECT    7    1    5   16                                                  
CONECT    8    2   10   12                                                  
CONECT    9    3   14   15                                                  
CONECT   10    6    8   14                                                  
CONECT   11    4   13   17                                                  
CONECT   12    5    8   20                                                  
CONECT   13   11   15   18                                                  
CONECT   14    9   10   20                                                  
CONECT   15    9   13   19                                                  
CONECT   16    7                                                            
CONECT   17   11                                                            
CONECT   18   13                                                            
CONECT   19    6   15                                                       
CONECT   20   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
4',7,8-Trihydroxypterocarpan	HMDB
4-Hydroxydemethylmedicarpin	HMDB
6a,11a-Dihydro-6H-benzofuro[3,2-c][1]benzopyran-3,4,9-triol	HMDB

Chemical Formula

C₁₅H₁₂O₅

Average Mass

272.2528 Da

Monoisotopic Mass

272.06847 Da

IUPAC Name

8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,6,14-triol

Traditional Name

8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,6,14-triol

CAS Registry Number

61255-58-1

SMILES

OC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2

InChI Identifier

InChI=1S/C15H12O5/c16-7-1-2-8-10-6-19-15-9(3-4-11(17)13(15)18)14(10)20-12(8)5-7/h1-5,10,14,16-18H,6H2

InChI Key

CLHTZHIBHTWFEM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Medicago sativa	FooDB	KNAPSACK
Melilotus alba	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

Not Available

Substituents

Not Available

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	1.87	ALOGPS
logP	2.06	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.56 m³·mol⁻¹	ChemAxon
Polarizability	27.03 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

HMDB0034002

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012236

KNApSAcK ID

C00009612

Chemspider ID

24843014

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257457

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,4,9-Trihydroxypterocarpan (NP0047813)

MOL for NP0047813 (3,4,9-Trihydroxypterocarpan)

3D MOL for NP0047813 (3,4,9-Trihydroxypterocarpan)

3D SDF for NP0047813 (3,4,9-Trihydroxypterocarpan)

3D-SDF for NP0047813 (3,4,9-Trihydroxypterocarpan)

PDB for NP0047813 (3,4,9-Trihydroxypterocarpan)

3D PDB for NP0047813 (3,4,9-Trihydroxypterocarpan)

SMILES for NP0047813 (3,4,9-Trihydroxypterocarpan)

INCHI for NP0047813 (3,4,9-Trihydroxypterocarpan)

Structure for NP0047813 (3,4,9-Trihydroxypterocarpan)

3D Structure for NP0047813 (3,4,9-Trihydroxypterocarpan)