Showing NP-Card for 7-Hexadecenoic acid (NP0046327)

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Record Information
Version2.0
Created at2022-03-17 19:56:15 UTC
Updated at2022-03-17 19:56:15 UTC
NP-MRD IDNP0046327
Secondary Accession NumbersNone
Natural Product Identification
Common Name7-Hexadecenoic acid
DescriptionHypogeic acid, also known as 16:1 CIS7 or C16:1(N=9), 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. Hypogeic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Hypogeic acid has been detected, but not quantified in, peanuts. This could make hypogeic acid a potential biomarker for the consumption of these foods. Hypogeic acid, with regard to humans, has been linked to the inborn metabolic disorder isovaleric acidemia. 7-Hexadecenoic acid is found in Hippophae rhamnoides and Mangifera indica. 7-Hexadecenoic acid was first documented in 2003 (PMID: 14641595). A C16 fatty acid having a (Z)-double bond at the 7-position; marker of early life stage mortality in trout and of physiologically active autotrophic bacteria in complex microbial communities (PMID: 20218500).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046327 (7-Hexadecenoic acid)

LMFA01030055
  Mrv1652303312018252D          

 18 17  0  0  0  0            999 V2000
   11.4304    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1448    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8594    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5739    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2884    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0030    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7175    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4320    5.2476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7175    6.4851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6054    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8908    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1763    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4619    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7474    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0329    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3184    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6039    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8895    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  7  9  2  0  0  0  0
  1 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 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
M  END
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3D MOL for NP0046327 (7-Hexadecenoic acid)

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3D SDF for NP0046327 (7-Hexadecenoic acid)
LMFA01030055
  Mrv1652303312018252D          

 18 17  0  0  0  0            999 V2000
   11.4304    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1448    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8594    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5739    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2884    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0030    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7175    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4320    5.2476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7175    6.4851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6054    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8908    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1763    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4619    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7474    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0329    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3184    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6039    5.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8895    5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  7  9  2  0  0  0  0
  1 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 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
M  END
> <DATABASE_ID>
NP0046327

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h9-10H,2-8,11-15H2,1H3,(H,17,18)/b10-9-

> <INCHI_KEY>
PJHOFUXBXJNUAC-KTKRTIGZSA-N

> <FORMULA>
C16H30O2

> <MOLECULAR_WEIGHT>
254.4082

> <EXACT_MASS>
254.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
32.870219879579025

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(7Z)-hexadec-7-enoic acid

> <ALOGPS_LOGP>
6.74

> <JCHEM_LOGP>
5.894661121

> <ALOGPS_LOGS>
-5.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.885823668538633

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
78.20019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.37e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hexadecenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0046327 (7-Hexadecenoic acid)
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PDB for NP0046327 (7-Hexadecenoic acid)
HEADER    PROTEIN                                 31-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LMFA01030055                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAR-20         0                                  
HETATM    1  C   UNK     0      21.337  10.566   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.670   9.796   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.004  10.566   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.338   9.796   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.672  10.566   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.006   9.796   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.339  10.566   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      30.673   9.796   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      29.339  12.106   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      19.797  10.566   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.463   9.796   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.129  10.566   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.796   9.796   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.462  10.566   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.128   9.796   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.794  10.566   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.461   9.796   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.127  10.566   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

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3D PDB for NP0046327 (7-Hexadecenoic acid)
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SMILES for NP0046327 (7-Hexadecenoic acid)
CCCCCCCC\C=C/CCCCCC(O)=O
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INCHI for NP0046327 (7-Hexadecenoic acid)
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h9-10H,2-8,11-15H2,1H3,(H,17,18)/b10-9-
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View in JSmol
Synonyms
ValueSource
(Z)-7-Hexadecenoic acidChEBI
16:1 cis7ChEBI
7-Hexadecenoic acidChEBI
C16:1(N=9)ChEBI
(Z)-7-HexadecenoateGenerator
7-HexadecenoateGenerator
HypogeateGenerator
7Z-PalmitoleateHMDB
Hypogeic acidChEBI
Chemical FormulaC16H30O2
Average Mass254.4082 Da
Monoisotopic Mass254.22458 Da
IUPAC Name(7Z)-hexadec-7-enoic acid
Traditional Name7-hexadecenoic acid
CAS Registry Number2416-19-5
SMILES
CCCCCCCC\C=C/CCCCCC(O)=O
InChI Identifier
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h9-10H,2-8,11-15H2,1H3,(H,17,18)/b10-9-
InChI KeyPJHOFUXBXJNUAC-KTKRTIGZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentLong-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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.74ALOGPS
logP5.89ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity78.2 m³·mol⁻¹ChemAxon
Polarizability32.87 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002186  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004011  
KNApSAcK IDNot Available
Chemspider ID4476987  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5318393  
PDB IDNot Available
ChEBI ID35465  
Good Scents IDNot Available
References
General References
  1. Knief C, Altendorf K, Lipski A: Linking autotrophic activity in environmental samples with specific bacterial taxa by detection of 13C-labelled fatty acids. Environ Microbiol. 2003 Nov;5(11):1155-67. doi: 10.1046/j.1462-2920.2003.00510.x. [PubMed:14641595  ] 
  2. Czesny S, Dettmers JM, Rinchard J, Dabrowski K: Linking egg thiamine and fatty acid concentrations of Lake Michigan lake trout with early life stage mortality. J Aquat Anim Health. 2009 Dec;21(4):262-71. doi: 10.1577/H07-056.1. [PubMed:20218500  ]