NP-MRD: Showing NP-Card for 2,3,9-Trimethoxypterocarpan (NP0047740)

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Record Information

Version

2.0

Created at

2022-03-17 20:45:10 UTC

Updated at

2022-03-17 20:45:10 UTC

NP-MRD ID

NP0047740

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3,9-Trimethoxypterocarpan

Description

2,3,9-Trimethoxypterocarpan, also known as 2-methoxyhomopterocarpin, 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, 2,3,9-trimethoxypterocarpan is considered to be a flavonoid lipid molecule. 2,3,9-Trimethoxypterocarpan is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 2,3,9-trimethoxypterocarpan has been detected, but not quantified in, common pea and pulses. 2,3,9-Trimethoxypterocarpan is found in Platymiscium floribundum. This could make 2,3,9-trimethoxypterocarpan a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061307212D          

 23 26  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
    6.5796   -3.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8689   -1.1420    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
    1.2608   -1.1491    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
    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
    3.1217   -0.6408    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
    5.3033   -2.6629    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
    3.2033   -2.0674    0.0000 C   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
    5.7559   -3.3526    0.0000 O   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
    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
  5  4  2  0  0  0  0
 10  4  1  0  0  0  0
 10  6  2  0  0  0  0
 11  5  1  0  0  0  0
 12  7  2  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  2  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 11  2  0  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
 17 16  2  0  0  0  0
 18 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19  1  1  0  0  0  0
 19 10  1  0  0  0  0
 20  2  1  0  0  0  0
 20 16  1  0  0  0  0
 21  3  1  0  0  0  0
 21 17  1  0  0  0  0
 22  9  1  0  0  0  0
 22 14  1  0  0  0  0
 23 15  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047740

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C1COC3=CC(OC)=C(OC)C=C3C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O5/c1-19-10-4-5-11-13-9-22-14-8-17(21-3)16(20-2)7-12(14)18(13)23-15(11)6-10/h4-8,13,18H,9H2,1-3H3

> <INCHI_KEY>
XCRBPIBUMBLGCZ-UHFFFAOYSA-N

> <FORMULA>
C18H18O5

> <MOLECULAR_WEIGHT>
314.3325

> <EXACT_MASS>
314.115423686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.458241511808026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5,14-trimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
2.497446186666666

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.177133946026918

> <JCHEM_POLAR_SURFACE_AREA>
46.150000000000006

> <JCHEM_REFRACTIVITY>
84.00659999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5,14-trimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene

> <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      -1.753  -4.262   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.282  -6.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.822  -2.132   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.985  -2.851   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       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.362  -5.059   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.827  -1.196   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  -2.978   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       9.899  -4.971   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.592  -3.595   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.979  -3.859   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.744  -6.258   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.129  -3.507   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.365  -1.108   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.016  -5.061   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4    5   10                                                       
CONECT    5    4   11                                                       
CONECT    6   10   15                                                       
CONECT    7   12   16                                                       
CONECT    8   14   17                                                       
CONECT    9   13   22                                                       
CONECT   10    4    6   19                                                  
CONECT   11    5   13   15                                                  
CONECT   12    7   14   18                                                  
CONECT   13    9   11   18                                                  
CONECT   14    8   12   22                                                  
CONECT   15    6   11   23                                                  
CONECT   16    7   17   20                                                  
CONECT   17    8   16   21                                                  
CONECT   18   12   13   23                                                  
CONECT   19    1   10                                                       
CONECT   20    2   16                                                       
CONECT   21    3   17                                                       
CONECT   22    9   14                                                       
CONECT   23   15   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
239-Trimethoxypterocarpan	HMDB
2-Methoxyhomopterocarpin	HMDB

Chemical Formula

C₁₈H₁₈O₅

Average Mass

314.3325 Da

Monoisotopic Mass

314.11542 Da

IUPAC Name

4,5,14-trimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene

Traditional Name

4,5,14-trimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene

CAS Registry Number

56782-49-1

SMILES

COC1=CC2=C(C=C1)C1COC3=CC(OC)=C(OC)C=C3C1O2

InChI Identifier

InChI=1S/C18H18O5/c1-19-10-4-5-11-13-9-22-14-8-17(21-3)16(20-2)7-12(14)18(13)23-15(11)6-10/h4-8,13,18H,9H2,1-3H3

InChI Key

XCRBPIBUMBLGCZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pisum sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Platymiscium floribundum	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	3.28	ALOGPS
logP	2.5	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.01 m³·mol⁻¹	ChemAxon
Polarizability	33.46 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

HMDB0033787

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011946

KNApSAcK ID

C00009622

Chemspider ID

9326267

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11151159

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2,3,9-Trimethoxypterocarpan (NP0047740)

MOL for NP0047740 (2,3,9-Trimethoxypterocarpan)

3D MOL for NP0047740 (2,3,9-Trimethoxypterocarpan)

3D SDF for NP0047740 (2,3,9-Trimethoxypterocarpan)

3D-SDF for NP0047740 (2,3,9-Trimethoxypterocarpan)

PDB for NP0047740 (2,3,9-Trimethoxypterocarpan)

3D PDB for NP0047740 (2,3,9-Trimethoxypterocarpan)

SMILES for NP0047740 (2,3,9-Trimethoxypterocarpan)

INCHI for NP0047740 (2,3,9-Trimethoxypterocarpan)

Structure for NP0047740 (2,3,9-Trimethoxypterocarpan)

3D Structure for NP0047740 (2,3,9-Trimethoxypterocarpan)