Sapienic acid

MUFA16:1Ω-10

  Overview

Stats

MUFA
Type
16
Carbons
1
Double bonds
0
Bis-allylic sites
254.41
Weight · g/mol
—
Melting point
C16H30O2
Formula

Also known as

IUPAC (Z)-hexadec-6-enoic acid

  At a Glance

Key Points

The signature fatty acid of human sebum — unique to humans (named from 'sapiens').

Source

Made in the body (endogenous synthesis); little comes from food.

Type

Long-chain monounsaturated fatty acid with 16 carbons and one cis double bond, an omega-10 fatty acid.

Identification

  Synonyms

Common Name Sapienic acid
IUPAC Name (Z)-hexadec-6-enoic acid
Traditional Name —
Other Synonyms No other synonyms recorded.

  External IDs

General References
Wikipedia Sapienic_acid
Lipids
Lipid Maps LMFA01030267
Lipid Bank —
Swiss Lipids 000000550
PlantFA ID —
Food & Nutrition
FooDB —
INFOODS —
Chemistry / Compounds
PubChem CID 5312419
CAS 17004-51-2
ChEBI 76244
ChEMBL —
ChemSpider 4471844
InChIKey —
ZINC ID ZINC000085617707
NIKKAJI ID J1.257.605F
PDBe 8Z9
UCI (UniChem) 27309341
SureChEMBL 1302049
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0340877
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS3251
BioCyc/MetaCyc CPD-14393
MetaNetX ID MNXM15061
BiGG ID —
KEGG C21942
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD117379
Clinical & Medical
SNOMED-CT —
MeSH C093821
NCIt Code C68382
Regulatory
NIH UNII (USA) 6460S1EJ28
FDA SRS (USA) 6460S1EJ28
NHPID (Canada) —
DTXSID (USA) DTXSID50904584
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-046-857-334
eMolecules —
Mcule —
ChemicalBook CB1961311
MedChemExpress HY-130187

Isomers of 16:1 (4)

Other fatty acids sharing the 16:1 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Sapienic acid
(Z)-hexadec-6-enoic acid
 6Z —
5312419
Category —
Conjugation Type —
SMILES CCCCCCCCC/C=C\CCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Positional (3)
Palmitoleic acid
(Z)-hexadec-9-enoic acid
 9Z —
445638
Category —
Conjugation Type —
SMILES CCCCCC\C=C/CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Hypogeic acid
(Z)-hexadec-7-enoic acid
 7Z —
5318393
Category —
Conjugation Type —
SMILES CCCCCCCC\C=C/CCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Palmitelaidic acid
(9E)-hexadec-9-enoic acid
 9E Trans
5282745
Category —
Conjugation Type —
SMILES CCCCCC\C=C\CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.

Chemical Properties

Name(s):
Common Name Sapienic acid
Simple Notation 16:1
Notation 16:1(n-10)
IUPAC Name (Z)-hexadec-6-enoic acid
Structure:
Molecular C16H30O2
Structure CH3(CH2)5CH=CH(CH2)7COOH
SMILES CCCCCCCCC/C=C\CCCCC(=O)O
Cis / Trans cis
E-Z 6Z
Physical:
Weight 254.41 g/mol
Reactivity
Double Bonds 1
Bis-Allylic Carbons 0
Beta-Oxidation
Beta Oxidation Cycles 7
ATP Yield (Net) 104.5 ATP