NP-MRD: Showing NP-Card for Demethylmedicarpin (NP0047837)

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Record Information

Version

2.0

Created at

2022-03-17 20:46:46 UTC

Updated at

2022-03-17 20:46:47 UTC

NP-MRD ID

NP0047837

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Demethylmedicarpin

Description

8,17-Dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol 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. 8,17-Dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol has been detected, but not quantified in, a few different foods, such as common beans, mung beans, and scarlet beans. Demethylmedicarpin is found in Erythrina abyssinica, Erythrina crista-galli , Erythrina fusca, Erythrina latissima, Erythrina poeppigiana , Erythrina sandwicensis, Melilotus alba, Pachyrrhizus erosus , Paraburkholderia phymatum, Psophocarpus tetragonolobus and Trifolium repens . This could make 8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309191708432D          

 19 22  0  0  0  0            999 V2000
    0.5275   -1.5272    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
    1.2608   -1.1491    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
    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
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  8  2  1  0  0  0  0
  8  5  2  0  0  0  0
  9  1  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  5  1  0  0  0  0
 13 11  2  0  0  0  0
 14  6  1  0  0  0  0
 14 10  2  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18  7  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047837

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O4/c16-8-2-4-11-13(5-8)18-7-12-10-3-1-9(17)6-14(10)19-15(11)12/h1-6,12,15-17H,7H2

> <INCHI_KEY>
ODMIEGVTNZNSLD-UHFFFAOYSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.2534

> <EXACT_MASS>
256.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.150653248401376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11,13,15-hexaene-5,14-diol

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
2.3633293403333324

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.792877417503597

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.180799963142011

> <JCHEM_PKA_STRONGEST_BASIC>
-4.587232188183343

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
68.5788

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11,13,15-hexaene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-SEP-17         0                                  
HETATM    1  C   UNK     0       0.985  -2.851   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       2.353  -2.145   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       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.827  -1.196   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.592  -3.595   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.911  -4.389   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.649  -2.977   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.517  -3.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.135  -2.572   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.210  -2.396   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.576  -4.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.980  -3.859   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.129  -3.507   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.365  -1.108   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.016  -5.061   0.000  0.00  0.00           O+0
CONECT    1    3    9                                                       
CONECT    2    4    8                                                       
CONECT    3    1   10                                                       
CONECT    4    2   11                                                       
CONECT    5    8   13                                                       
CONECT    6    9   14                                                       
CONECT    7   12   18                                                       
CONECT    8    2    5   16                                                  
CONECT    9    1    6   17                                                  
CONECT   10    3   12   14                                                  
CONECT   11    4   13   15                                                  
CONECT   12    7   10   15                                                  
CONECT   13    5   11   18                                                  
CONECT   14    6   10   19                                                  
CONECT   15   11   12   19                                                  
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18    7   13                                                       
CONECT   19   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₄

Average Mass

256.2534 Da

Monoisotopic Mass

256.07356 Da

IUPAC Name

8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11,13,15-hexaene-5,14-diol

Traditional Name

8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11,13,15-hexaene-5,14-diol

CAS Registry Number

61135-91-9

SMILES

OC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2

InChI Identifier

InChI=1S/C15H12O4/c16-8-2-4-11-13(5-8)18-7-12-10-3-1-9(17)6-14(10)19-15(11)12/h1-6,12,15-17H,7H2

InChI Key

ODMIEGVTNZNSLD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Erythrina abyssinica	LOTUS Database	35616633
Erythrina crista-galli	Plant	KNApSAcK
Erythrina fusca	LOTUS Database	35616633
Erythrina latissima	Plant	KNApSAcK
Erythrina poeppigiana	Plant	KNApSAcK
Erythrina sandwicensis	Plant	KNApSAcK
Melilotus alba	Plant	KNApSAcK
Pachyrrhizus erosus	Plant	KNApSAcK
Paraburkholderia phymatum	-	KNApSAcK
Phaseolus coccineus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Psophocarpus tetragonolobus	Plant	KNApSAcK
Trifolium repens	Plant	KNApSAcK
Vigna radiata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070029 )
a small molecule (CPD-4402 )

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	2.59	ALOGPS
logP	2.36	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.18	ChemAxon
pKa (Strongest Basic)	-4.6	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	0	ChemAxon
Refractivity	68.58 m³·mol⁻¹	ChemAxon
Polarizability	26.15 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

HMDB0138504

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012305

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

3347979

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Demethylmedicarpin (NP0047837)

MOL for NP0047837 (Demethylmedicarpin)

3D MOL for NP0047837 (Demethylmedicarpin)

3D SDF for NP0047837 (Demethylmedicarpin)

3D-SDF for NP0047837 (Demethylmedicarpin)

PDB for NP0047837 (Demethylmedicarpin)

3D PDB for NP0047837 (Demethylmedicarpin)

SMILES for NP0047837 (Demethylmedicarpin)

INCHI for NP0047837 (Demethylmedicarpin)

Structure for NP0047837 (Demethylmedicarpin)

3D Structure for NP0047837 (Demethylmedicarpin)