NP-MRD: Showing NP-Card for 9-hydroxyoctadeca-10,14-dien-12-ynoic acid (NP0153862)

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Record Information

Version

1.0

Created at

2022-09-02 10:35:29 UTC

Updated at

2022-09-02 10:35:29 UTC

NP-MRD ID

NP0153862

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-hydroxyoctadeca-10,14-dien-12-ynoic acid

Description

9-Hydroxyoctadeca-10,14-dien-12-ynoic acid belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 9-hydroxyoctadeca-10,14-dien-12-ynoic acid is found in Cantharellus cibarius. It was first documented in 2012 (PMID: 22342624). Based on a literature review very few articles have been published on 9-hydroxyoctadeca-10,14-dien-12-ynoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022212352D          

 21 20  0  0  0  0            999 V2000
    0.6632    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    7.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    6.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  3  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153862

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC=CC#CC=CC(O)CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H28O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h4-5,11,14,17,19H,2-3,7,9-10,12-13,15-16H2,1H3,(H,20,21)

> <INCHI_KEY>
DFVZVNJGUDAZDP-UHFFFAOYSA-N

> <FORMULA>
C18H28O3

> <MOLECULAR_WEIGHT>
292.419

> <EXACT_MASS>
292.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.60275120742871

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxyoctadeca-10,14-dien-12-ynoic acid

> <ALOGPS_LOGP>
4.95

> <JCHEM_LOGP>
4.7757723919999995

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.322846377086144

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.676745397945889

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7827872092691752

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
89.39569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.15e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxyoctadeca-10,14-dien-12-ynoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.238  14.575   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.572  13.805   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.572  12.265   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.905  11.495   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.905   9.955   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.239   9.185   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.573   8.415   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.906   7.645   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.240   3.795   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      21.243   6.105   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      19.909   3.795   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
9-Hydroxyoctadeca-10,14-dien-12-ynoate	Generator

Chemical Formula

C₁₈H₂₈O₃

Average Mass

292.4190 Da

Monoisotopic Mass

292.20384 Da

IUPAC Name

9-hydroxyoctadeca-10,14-dien-12-ynoic acid

Traditional Name

9-hydroxyoctadeca-10,14-dien-12-ynoic acid

CAS Registry Number

Not Available

SMILES

CCCC=CC#CC=CC(O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H28O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h4-5,11,14,17,19H,2-3,7,9-10,12-13,15-16H2,1H3,(H,20,21)

InChI Key

DFVZVNJGUDAZDP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cantharellus cibarius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	4.95	ALOGPS
logP	4.78	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	89.4 m³·mol⁻¹	ChemAxon
Polarizability	36.6 Å³	ChemAxon
Number of Rings	0	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21230656

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72738951

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hong SS, Lee JH, Jeong W, Kim N, Jin HZ, Hwang BY, Lee HJ, Lee SJ, Jang DS, Lee D: Acetylenic acid analogues from the edible mushroom Chanterelle (Cantharellus cibarius) and their effects on the gene expression of peroxisome proliferator-activated receptor-gamma target genes. Bioorg Med Chem Lett. 2012 Mar 15;22(6):2347-9. doi: 10.1016/j.bmcl.2012.01.070. Epub 2012 Jan 28. [PubMed:22342624 ]
LOTUS database [Link]

Showing NP-Card for 9-hydroxyoctadeca-10,14-dien-12-ynoic acid (NP0153862)

MOL for NP0153862 (9-hydroxyoctadeca-10,14-dien-12-ynoic acid)

3D MOL for NP0153862 (9-hydroxyoctadeca-10,14-dien-12-ynoic acid)

3D SDF for NP0153862 (9-hydroxyoctadeca-10,14-dien-12-ynoic acid)

3D-SDF for NP0153862 (9-hydroxyoctadeca-10,14-dien-12-ynoic acid)

PDB for NP0153862 (9-hydroxyoctadeca-10,14-dien-12-ynoic acid)

3D PDB for NP0153862 (9-hydroxyoctadeca-10,14-dien-12-ynoic acid)

SMILES for NP0153862 (9-hydroxyoctadeca-10,14-dien-12-ynoic acid)

INCHI for NP0153862 (9-hydroxyoctadeca-10,14-dien-12-ynoic acid)

Structure for NP0153862 (9-hydroxyoctadeca-10,14-dien-12-ynoic acid)

3D Structure for NP0153862 (9-hydroxyoctadeca-10,14-dien-12-ynoic acid)