NP-MRD: Showing NP-Card for 10Z-Heptadecenoic acid (NP0339556)

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Record Information

Version

2.0

Created at

2024-09-11 22:25:39 UTC

Updated at

2024-09-11 22:25:39 UTC

NP-MRD ID

NP0339556

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10Z-Heptadecenoic acid

Description

10Z-Heptadecenoic acid, also known as 17:1 N-7 cis or cis-tetradec-10-enoic 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. It occurs as a trace component of the fat and milkfat of ruminants, but it does not occur in any natural animal or vegetable fat at concentrations over half a percent. Salts and esters of heptadecanoic acid are called heptadecanoates. 10Z-Heptadecenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 10Z-Heptadecenoic acid is a monounsaturated fatty acid with an unsaturated double bond at the 10th carbon. Heptadecanoic acid, or margaric acid, is a saturated fatty acid. 10Z-Heptadecenoic acid was first documented in 2005 (PMID: 16246309). Its molecular formula is CH3(CH2)15COOH (PMID: 24930002) (PMID: 18657232) (PMID: 18827358) (PMID: 18972241).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304032007052D          

 19 18  0  0  0  0            999 V2000
 9998.1761 9999.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8911 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6079 9999.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3227 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0383 9999.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8632 9999.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5767 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2923 9999.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.0079 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.7214 9999.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.4370 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.1526 9999.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4613 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7466 9999.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0318 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3168 9999.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6020 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8873 9999.3864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.602010000.6235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  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
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339556

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC\C=C/CCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h7-8H,2-6,9-16H2,1H3,(H,18,19)/b8-7-

> <INCHI_KEY>
GDTXICBNEOEPAZ-FPLPWBNLSA-N

> <FORMULA>
C17H32O2

> <MOLECULAR_WEIGHT>
268.4348

> <EXACT_MASS>
268.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
34.9773998324187

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10Z)-heptadec-10-enoic acid

> <ALOGPS_LOGP>
7.21

> <JCHEM_LOGP>
6.339229786

> <ALOGPS_LOGS>
-6.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.021116877046745

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
82.80119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.26e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10Z)-heptadec-10-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0    8663.2628665.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.5978666.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.9358665.521   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8667.2698666.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8668.6058665.521   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8670.1458665.521   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8671.4778666.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8672.8128665.521   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8674.1488666.290   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8675.4808665.521   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8676.8168666.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8678.1528665.521   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8661.9288666.290   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.5948665.521   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8659.2598666.290   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8657.9258665.521   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8656.5908666.290   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    8655.2568665.521   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0    8656.5908667.831   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
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                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Value	Source
(10Z)-10-Heptadecenoic acid	ChEBI
(10Z)-Heptadec-10-enoic acid	ChEBI
17:1 N-7 cis	ChEBI
C17:1 N-7 cis	ChEBI
cis-10-Heptadecenoic acid	ChEBI
cis-Tetradec-10-enoic acid	ChEBI
(10Z)-10-Heptadecenoate	Generator
(10Z)-Heptadec-10-enoate	Generator
cis-10-Heptadecenoate	Generator
cis-Tetradec-10-enoate	Generator
10Z-Heptadecenoate	Generator
(Z)-10-Heptadecenoic acid	HMDB
10-cis-Heptadecenoic acid	HMDB
10-Heptadecenoate (17:1n7)	HMDB
FA(17:1(10Z))	HMDB
10Z-Heptadecenoic acid	ChEBI
10-Heptadecenoate	HMDB
FA(17:1n7)	HMDB
(10Z)-Heptadecenoate	Generator

Chemical Formula

C₁₇H₃₂O₂

Average Mass

268.4348 Da

Monoisotopic Mass

268.24023 Da

IUPAC Name

(10Z)-heptadec-10-enoic acid

Traditional Name

(10Z)-heptadec-10-enoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC\C=C/CCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C17H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h7-8H,2-6,9-16H2,1H3,(H,18,19)/b8-7-

InChI Key

GDTXICBNEOEPAZ-FPLPWBNLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

10-heptadecenoic acid (CHEBI:75094 )
Unsaturated fatty acids (LMFA01030283 )

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	7.21	ALOGPS
logP	6.34	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	5.02	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	82.8 m³·mol⁻¹	ChemAxon
Polarizability	34.98 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0060038

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4471860

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5312435

PDB ID

Not Available

ChEBI ID

75094

Good Scents ID

Not Available

References

General References

Tanemossu SA, Franke K, Arnold N, Schmidt J, Wabo HK, Tane P, Wessjohann LA: Rare biscoumarin derivatives and flavonoids from Hypericum riparium. Phytochemistry. 2014 Sep;105:171-7. doi: 10.1016/j.phytochem.2014.05.008. Epub 2014 Jun 11. [PubMed:24930002 ]
Jambor de Sousa UL, Koss MD, Fillies M, Gahl A, Scheeder MR, Cardoso MC, Leonhardt H, Geary N, Langhans W, Leonhardt M: CPT1alpha over-expression increases long-chain fatty acid oxidation and reduces cell viability with incremental palmitic acid concentration in 293T cells. Biochem Biophys Res Commun. 2005 Dec 16;338(2):757-61. doi: 10.1016/j.bbrc.2005.10.016. Epub 2005 Oct 13. [PubMed:16246309 ]
Goepfert S, Vidoudez C, Tellgren-Roth C, Delessert S, Hiltunen JK, Poirier Y: Peroxisomal Delta(3),Delta(2)-enoyl CoA isomerases and evolution of cytosolic paralogues in embryophytes. Plant J. 2008 Dec;56(5):728-42. doi: 10.1111/j.1365-313X.2008.03635.x. Epub 2008 Jul 23. [PubMed:18657232 ]
Fukuzawa M, Yamaguchi R, Hide I, Chen Z, Hirai Y, Sugimoto A, Yasuhara T, Nakata Y: Possible involvement of long chain fatty acids in the spores of Ganoderma lucidum (Reishi Houshi) to its anti-tumor activity. Biol Pharm Bull. 2008 Oct;31(10):1933-7. doi: 10.1248/bpb.31.1933. [PubMed:18827358 ]
Ozogul Y, Ozogul F, Cicek E, Polat A, Kuley E: Fat content and fatty acid compositions of 34 marine water fish species from the Mediterranean Sea. Int J Food Sci Nutr. 2009 Sep;60(6):464-75. doi: 10.1080/09637480701838175. [PubMed:18972241 ]

Showing NP-Card for 10Z-Heptadecenoic acid (NP0339556)

MOL for NP0339556 (10Z-Heptadecenoic acid)

3D MOL for NP0339556 (10Z-Heptadecenoic acid)

3D SDF for NP0339556 (10Z-Heptadecenoic acid)

3D-SDF for NP0339556 (10Z-Heptadecenoic acid)

PDB for NP0339556 (10Z-Heptadecenoic acid)

3D PDB for NP0339556 (10Z-Heptadecenoic acid)

SMILES for NP0339556 (10Z-Heptadecenoic acid)

INCHI for NP0339556 (10Z-Heptadecenoic acid)

Structure for NP0339556 (10Z-Heptadecenoic acid)

3D Structure for NP0339556 (10Z-Heptadecenoic acid)