NP-MRD: Showing NP-Card for 9-O-Methylcoumestrol (NP0047676)

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Record Information

Version

2.0

Created at

2022-03-17 20:44:05 UTC

Updated at

2022-03-17 20:44:05 UTC

NP-MRD ID

NP0047676

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-O-Methylcoumestrol

Description

2-Pentylpyridine, also known as fema 3383, belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms. 2-Pentylpyridine is a very strong basic compound (based on its pKa). 2-Pentylpyridine is a fat, fatty, and green tasting compound. Outside of the human body, 2-Pentylpyridine has been detected, but not quantified in, several different foods, such as sweet oranges, cereals and cereal products, yellow bell peppers, orange bell peppers, and green bell peppers. 9-O-Methylcoumestrol is found in Cicer anatolicum, Cicer canariensis, Cicer chorassanicum, Cicer cuneatum, Cicer echinospermum, Cicer microphyllum, Cicer nuristanicum, Cicer oxyodon, Cicer reticulatum, Cicer yamashitae, Dalbergia odorifera , Dalbergia oliveri, Dalbergia stevensonii, Melilotus messanensis, Myroxylon balsamum , Pisum sativum , Trifolium pratense and Trifolium repens . This could make 2-pentylpyridine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307132D          

 21 24  0  0  0  0            999 V2000
   -1.9532    2.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2891    2.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    3.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    2.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466    3.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2075    3.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601    2.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    2.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9407    3.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0128    2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    3.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    2.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365    3.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    4.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4838    2.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548    4.8202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2591    2.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312    4.1776    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
  8  2  1  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
  9  7  2  0  0  0  0
 10  5  1  0  0  0  0
 11  4  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  2  0  0  0  0
 13  7  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  2  0  0  0  0
 16 14  1  0  0  0  0
 17  8  1  0  0  0  0
 18 16  2  0  0  0  0
 19  1  1  0  0  0  0
 19  9  1  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
 21 12  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047676

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O5/c1-19-9-3-5-10-13(7-9)20-15-11-4-2-8(17)6-12(11)21-16(18)14(10)15/h2-7,17H,1H3

> <INCHI_KEY>
HHEZPZWGHDOWCQ-UHFFFAOYSA-N

> <FORMULA>
C16H10O5

> <MOLECULAR_WEIGHT>
282.2476

> <EXACT_MASS>
282.05282343

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.55305851630776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
2.543215378333333

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.115222554291015

> <JCHEM_PKA_STRONGEST_BASIC>
-4.223027562816092

> <JCHEM_POLAR_SURFACE_AREA>
68.9

> <JCHEM_REFRACTIVITY>
74.1018

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

> <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      -3.646   4.644   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.006   3.936   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.909   6.056   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.699   5.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.756   5.929   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.624   5.135   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.316   6.511   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.241   6.335   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.087   5.047   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.236   5.399   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.089   8.998   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.350   3.812   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.123   3.846   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.472   7.798   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    4    8                                                       
CONECT    3    5    9                                                       
CONECT    4    2   11                                                       
CONECT    5    3   10                                                       
CONECT    6    8   12                                                       
CONECT    7    9   13                                                       
CONECT    8    2    6   17                                                  
CONECT    9    3    7   19                                                  
CONECT   10    5   13   14                                                  
CONECT   11    4   12   15                                                  
CONECT   12    6   11   21                                                  
CONECT   13    7   10   20                                                  
CONECT   14   10   15   16                                                  
CONECT   15   11   14   20                                                  
CONECT   16   14   18   21                                                  
CONECT   17    8                                                            
CONECT   18   16                                                            
CONECT   19    1    9                                                       
CONECT   20   13   15                                                       
CONECT   21   12   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Value	Source
2-Amyl pyridine	HMDB
2-Amylpyridine	HMDB
2-N-Amylpyridine	HMDB
2-N-Pentylpyridine	HMDB
2-Pentyl-pyridine	HMDB
FEMA 3383	HMDB
12-O-Methylcoumestrol	HMDB
3-Hydroxy-9-methoxycoumestan	HMDB
4'-Methoxycoumestrol	HMDB
4'-O-Methylcoumestrol	HMDB
Methyl N-methylnipecotate	HMDB

Chemical Formula

C₁₆H₁₀O₅

Average Mass

282.2476 Da

Monoisotopic Mass

282.05282 Da

IUPAC Name

5-hydroxy-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

Traditional Name

5-hydroxy-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

CAS Registry Number

1690-62-6

SMILES

COC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2

InChI Identifier

InChI=1S/C16H10O5/c1-19-9-3-5-10-13(7-9)20-15-11-4-2-8(17)6-12(11)21-16(18)14(10)15/h2-7,17H,1H3

InChI Key

HHEZPZWGHDOWCQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cicer anatolicum	Plant	KNApSAcK
Cicer arietinum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cicer canariensis	Plant	KNApSAcK
Cicer chorassanicum	Plant	KNApSAcK
Cicer cuneatum	Plant	KNApSAcK
Cicer echinospermum	Plant	KNApSAcK
Cicer microphyllum	Plant	KNApSAcK
Cicer nuristanicum	Plant	KNApSAcK
Cicer oxyodon	Plant	KNApSAcK
Cicer reticulatum	Plant	KNApSAcK
Cicer yamashitae	Plant	KNApSAcK
Dalbergia odorifera	Plant	KNApSAcK
Dalbergia oliveri	Plant	KNApSAcK
Dalbergia stevensonii	Plant	KNApSAcK
Medicago sativa	FooDB	KNAPSACK
Melilotus messanensis	Plant	KNApSAcK
Myroxylon balsamum	Plant	KNApSAcK
Pisum sativum	Plant	KNApSAcK
Trifolium pratense	Plant	KNApSAcK
Trifolium repens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Not Available

Direct Parent

Pyridines and derivatives

Alternative Parents

Substituents

Pyridine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.85	ALOGPS
logP	2.54	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.1 m³·mol⁻¹	ChemAxon
Polarizability	28.55 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

HMDB0034893

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013469

KNApSAcK ID

Not Available

Chemspider ID

15924

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16800

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 9-O-Methylcoumestrol (NP0047676)

MOL for NP0047676 (9-O-Methylcoumestrol)

3D MOL for NP0047676 (9-O-Methylcoumestrol)

3D SDF for NP0047676 (9-O-Methylcoumestrol)

3D-SDF for NP0047676 (9-O-Methylcoumestrol)

PDB for NP0047676 (9-O-Methylcoumestrol)

3D PDB for NP0047676 (9-O-Methylcoumestrol)

SMILES for NP0047676 (9-O-Methylcoumestrol)

INCHI for NP0047676 (9-O-Methylcoumestrol)

Structure for NP0047676 (9-O-Methylcoumestrol)

3D Structure for NP0047676 (9-O-Methylcoumestrol)