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Record Information
Version2.0
Created at2022-09-07 00:49:56 UTC
Updated at2022-09-07 00:49:56 UTC
NP-MRD IDNP0240899
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-hydroxytricosanoic acid
Description2-Hydroxytricosanoic acid belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. 2-hydroxytricosanoic acid is found in Amphimedon compressa, Callyspongia fallax, Cervicornia cuspidifera, Smenospongia aurea and Tripneustes ventricosus. 2-hydroxytricosanoic acid was first documented in 1989 (PMID: 2747436). 2-Hydroxytricosanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 11253924) (PMID: 12934678).
Structure
Thumb
Synonyms
ValueSource
2-HydroxytricosanoateGenerator
Chemical FormulaC23H46O3
Average Mass370.6180 Da
Monoisotopic Mass370.34470 Da
IUPAC Name2-hydroxytricosanoic acid
Traditional Name2-hydroxytricosanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCC(O)C(O)=O
InChI Identifier
InChI=1S/C23H46O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(24)23(25)26/h22,24H,2-21H2,1H3,(H,25,26)
InChI KeyJZWLIRVAYJRWLN-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Amphimedon compressaLOTUS Database
Callyspongia fallaxLOTUS Database
Cervicornia cuspidiferaLOTUS Database
Smenospongia aureaLOTUS Database
Tripneustes ventricosusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very long-chain fatty acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • 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
logP8.82ALOGPS
logP8.5ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)4.26ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity110.78 m³·mol⁻¹ChemAxon
Polarizability50.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-8470
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound152915
PDB IDNot Available
ChEBI ID84858
Good Scents IDNot Available
References
General References
  1. Kang SS, Kim JS, Son KH, Kim HP, Chang HW: Cyclooxygenase-2 inhibitory cerebrosides from phytolaccae radix. Chem Pharm Bull (Tokyo). 2001 Mar;49(3):321-3. doi: 10.1248/cpb.49.321. [PubMed:11253924 ]
  2. Liu JK, Hu L, Dong ZJ: A glucosylceramide with a novel ceramide and three novel ceramides from the basidiomycete Cortinarius umidicola. Lipids. 2003 Jun;38(6):669-75. doi: 10.1007/s11745-003-1113-x. [PubMed:12934678 ]
  3. Carballeira NM, Lopez MR: On the isolation of 2-hydroxydocosanoic and 2-hydroxytricosanoic acids from the marine sponge Amphimedon compressa. Lipids. 1989 Jan;24(1):89-91. doi: 10.1007/BF02535272. [PubMed:2747436 ]
  4. LOTUS database [Link]