NP-MRD: Showing NP-Card for 4-Hydroxy-2,3,9-trimethoxypterocarpan (NP0047749)

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Record Information

Version

2.0

Created at

2022-03-17 20:45:20 UTC

Updated at

2022-03-17 20:45:20 UTC

NP-MRD ID

NP0047749

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Hydroxy-2,3,9-trimethoxypterocarpan

Description

1-Phenyl-1,3-heneicosanedione, also known as 1-benzoyl-2-eicosanone, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 1-Phenyl-1,3-heneicosanedione is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1-Phenyl-1,3-heneicosanedione has been detected, but not quantified in, fats and oils. 4-Hydroxy-2,3,9-trimethoxypterocarpan is found in Platymiscium floribundum. This could make 1-phenyl-1,3-heneicosanedione a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061307232D          

 24 27  0  0  0  0            999 V2000
    7.2186    1.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000    2.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894    0.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    5.0972    2.4741    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
    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
    4.3640    2.0960    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
    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
    0.6053    1.6029    0.0000 C   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
    6.5246    2.4062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5236    3.0295    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
    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
  5  4  2  0  0  0  0
  9  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  5  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  2  0  0  0  0
 14  7  1  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 11  1  0  0  0  0
 17 15  2  0  0  0  0
 18 14  2  0  0  0  0
 18 15  1  0  0  0  0
 19 15  1  0  0  0  0
 20  1  1  0  0  0  0
 20  9  1  0  0  0  0
 21  2  1  0  0  0  0
 21 14  1  0  0  0  0
 22  3  1  0  0  0  0
 22 18  1  0  0  0  0
 23  8  1  0  0  0  0
 23 17  1  0  0  0  0
 24 13  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047749

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c1-20-9-4-5-10-12-8-23-17-11(16(12)24-13(10)6-9)7-14(21-2)18(22-3)15(17)19/h4-7,12,16,19H,8H2,1-3H3

> <INCHI_KEY>
APDOGYRSSCEXNB-UHFFFAOYSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.3319

> <EXACT_MASS>
330.110338308

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
34.328817491213584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <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-hexaen-6-ol

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
2.1938808649999997

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.170456613586337

> <JCHEM_PKA_STRONGEST_BASIC>
-4.20409641636387

> <JCHEM_POLAR_SURFACE_AREA>
66.38000000000001

> <JCHEM_REFRACTIVITY>
85.9875

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.93e-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-hexaen-6-ol

> <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      13.475   3.659   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.560   5.567   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.100   1.528   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.737   2.247   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.368   1.542   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.515   4.618   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.360   4.456   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.895   0.593   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.810   3.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.073   2.374   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.205   3.168   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.587   1.969   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.146   3.913   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.822   4.367   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.975   1.704   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.742   3.256   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.512   1.793   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.130   2.992   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.282   0.329   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.179   4.492   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.977   5.655   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.408   2.904   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.357   0.505   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.706   4.457   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4    5    9                                                       
CONECT    5    4   10                                                       
CONECT    6    9   13                                                       
CONECT    7   11   14                                                       
CONECT    8   12   23                                                       
CONECT    9    4    6   20                                                  
CONECT   10    5   12   13                                                  
CONECT   11    7   16   17                                                  
CONECT   12    8   10   16                                                  
CONECT   13    6   10   24                                                  
CONECT   14    7   18   21                                                  
CONECT   15   17   18   19                                                  
CONECT   16   11   12   24                                                  
CONECT   17   11   15   23                                                  
CONECT   18   14   15   22                                                  
CONECT   19   15                                                            
CONECT   20    1    9                                                       
CONECT   21    2   14                                                       
CONECT   22    3   18                                                       
CONECT   23    8   17                                                       
CONECT   24   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
1-Benzoyl-2-eicosanone	HMDB
6a,11a-dihydro-2,3,9-Trimethoxy-6H-benzofuro[3,2-c][1]benzopyran-4-ol, 9ci	HMDB

Chemical Formula

C₁₈H₁₈O₆

Average Mass

330.3319 Da

Monoisotopic Mass

330.11034 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-hexaen-6-ol

Traditional Name

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

CAS Registry Number

56841-82-8

SMILES

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

InChI Identifier

InChI=1S/C18H18O6/c1-20-9-4-5-10-12-8-23-17-11(16(12)24-13(10)6-9)7-14(21-2)18(22-3)15(17)19/h4-7,12,16,19H,8H2,1-3H3

InChI Key

APDOGYRSSCEXNB-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	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
Aryl alkyl ketone
Benzoyl
1,3-diketone
Benzenoid
1,3-dicarbonyl compound
Monocyclic benzene moiety
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	2.61	ALOGPS
logP	2.19	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.17	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.99 m³·mol⁻¹	ChemAxon
Polarizability	34.33 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

HMDB0035585

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014277

KNApSAcK ID

Not Available

Chemspider ID

14602054

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23036629

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-Hydroxy-2,3,9-trimethoxypterocarpan (NP0047749)

MOL for NP0047749 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

3D MOL for NP0047749 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

3D SDF for NP0047749 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

3D-SDF for NP0047749 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

PDB for NP0047749 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

3D PDB for NP0047749 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

SMILES for NP0047749 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

INCHI for NP0047749 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

Structure for NP0047749 (4-Hydroxy-2,3,9-trimethoxypterocarpan)

3D Structure for NP0047749 (4-Hydroxy-2,3,9-trimethoxypterocarpan)