Showing NP-Card for 11Z-hexadecenoic acid (NP0339578)

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Record Information
Version2.0
Created at2024-09-11 22:32:34 UTC
Updated at2024-09-11 22:32:34 UTC
NP-MRD IDNP0339578
Secondary Accession NumbersNone
Natural Product Identification
Common Name11Z-hexadecenoic acid
Description11Z-hexadecenoic acid, also known as (Z)-11-hexadecenoate, 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. 11Z-hexadecenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 11Z-hexadecenoic acid was first documented in 2010 (PMID: 20691782). A C16, monounsaturated fatty acid with a double bond at position 11; a key intermediate in silkworm pheromone biosynthesis.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339578 (11Z-hexadecenoic acid)

  Mrv1652309272007392D          

 18 17  0  0  0  0            999 V2000
 9999.736810000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.451910001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.166810000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.882010001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.595610000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.311310001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.136310001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.852010000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.567710001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.281310000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.997010001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.022010001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.307110000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.592210001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.877110000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.162410001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.447510000.5986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.162410001.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  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  1  0  0  0  0
  6  7  2  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
 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
 16 18  2  0  0  0  0
M  END
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3D MOL for NP0339578 (11Z-hexadecenoic acid)

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3D SDF for NP0339578 (11Z-hexadecenoic acid)
  Mrv1652309272007392D          

 18 17  0  0  0  0            999 V2000
 9999.736810000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.451910001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.166810000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.882010001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.595610000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.311310001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.136310001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.852010000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.567710001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.281310000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.997010001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.022010001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.307110000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.592210001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.877110000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.162410001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.447510000.5986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.162410001.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  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  1  0  0  0  0
  6  7  2  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
 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
 16 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339578

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC\C=C/CCCCCCCCCC(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/h5-6H,2-4,7-15H2,1H3,(H,17,18)/b6-5-

> <INCHI_KEY>
JGMYDQCXGIMHLL-WAYWQWQTSA-N

> <FORMULA>
C16H30O2

> <MOLECULAR_WEIGHT>
254.414

> <EXACT_MASS>
254.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
32.92488825484392

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11Z)-hexadec-11-enoic acid

> <ALOGPS_LOGP>
6.71

> <JCHEM_LOGP>
5.894661121

> <ALOGPS_LOGS>
-5.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019655228562

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
78.20019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.47e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-hexadecenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339578 (11Z-hexadecenoic acid)
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PDB for NP0339578 (11Z-hexadecenoic acid)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8666.1758667.784   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.5108668.552   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8668.8458667.784   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8670.1808668.552   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8671.5128667.784   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8672.8488668.552   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8674.3888668.552   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8675.7248667.784   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8677.0608668.552   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8678.3928667.784   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8679.7288668.552   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.8418668.552   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.5078667.784   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.1728668.552   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.8378667.784   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8659.5038668.552   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8658.1698667.784   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    8659.5038670.094   0.000  0.00  0.00           O+0
CONECT    1    2   12                                                       
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                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

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3D PDB for NP0339578 (11Z-hexadecenoic acid)
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SMILES for NP0339578 (11Z-hexadecenoic acid)
CCCC\C=C/CCCCCCCCCC(O)=O
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INCHI for NP0339578 (11Z-hexadecenoic acid)
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h5-6H,2-4,7-15H2,1H3,(H,17,18)/b6-5-
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View in JSmol
Synonyms
ValueSource
(Z)-11-Hexadecenoic acidChEBI
11-Hexadecenoic acidChEBI
(Z)-11-HexadecenoateGenerator
11-HexadecenoateGenerator
11Z-HexadecenoateGenerator
cis-PalmitvaccenateGenerator
(11Z)-Hexadecenoic acidHMDB
FA(16:1(11Z))HMDB
(11Z)-11-Hexadecenoic acidPhytoBank
Hexadec-11(Z)-enoic acidPhytoBank
cis-11-Hexadecenoic acidPhytoBank
delta11-Hexadecenoic acidPhytoBank
Δ11-Hexadecenoic acidPhytoBank
Chemical FormulaC16H30O2
Average Mass254.4140 Da
Monoisotopic Mass254.22458 Da
IUPAC Name(11Z)-hexadec-11-enoic acid
Traditional Name11-hexadecenoic acid
CAS Registry NumberNot Available
SMILES
CCCC\C=C/CCCCCCCCCC(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/h5-6H,2-4,7-15H2,1H3,(H,17,18)/b6-5-
InChI KeyJGMYDQCXGIMHLL-WAYWQWQTSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot 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.
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
logP6.71ALOGPS
logP5.89ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity78.2 m³·mol⁻¹ChemAxon
Polarizability32.92 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0061979  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312414  
PDB IDNot Available
ChEBI ID35464  
Good Scents IDNot Available
References
General References
  1. Wang HL, Lienard MA, Zhao CH, Wang CZ, Lofstedt C: Neofunctionalization in an ancestral insect desaturase lineage led to rare Delta6 pheromone signals in the Chinese tussah silkworm. Insect Biochem Mol Biol. 2010 Oct;40(10):742-51. doi: 10.1016/j.ibmb.2010.07.009.  Epub 2010 Aug 5. [PubMed:20691782  ]