RICINOLEIC ACID

General Information

From www.fda.gov

2D Structure
CID	643684
IUPAC Name	(Z,12R)-12-hydroxyoctadec-9-enoic acid
InChI	InChI=1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-/t17-/m1/s1
InChI Key	WBHHMMIMDMUBKC-QJWNTBNXSA-N
Canonical SMILES	CCCCCCC(CC=CCCCCCCCC(=O)O)O
Molecular Formula	C18H34O3
Wikipedia	(9Z)-12-hydroxyoctadec-9-enoic acid

From Pubchem

Property Name	Property Value
Molecular Weight	298.467
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	15
Complexity	261.0
CACTVS Substructure Key Fingerprint	A A A D c f B 4 M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A C A A A C B S g g A I C C A A A A g C I A C D S C A A A A A A g A A A I C A E A A A g A E B I A A Q A A Q A A E w A A I A A O I y K C A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area	57.5
Monoisotopic Mass	298.251
Exact Mass	298.251
XLogP3	None
XLogP3-AA	5.7
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	21
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Isotope Atom Count	0
Covalently-Bonded Unit Count	1

From Pubchem

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.8153
Human Intestinal Absorption	HIA+	0.9935
Caco-2 Permeability	Caco2+	0.7403
P-glycoprotein Substrate	Substrate	0.5260
P-glycoprotein Inhibitor	Non-inhibitor	0.9580
P-glycoprotein Inhibitor	Non-inhibitor	0.7879
Renal Organic Cation Transporter	Non-inhibitor	0.9265
Distribution
Subcellular localization	Mitochondria	0.6237
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.8011
CYP450 2D6 Substrate	Non-substrate	0.8869
CYP450 3A4 Substrate	Non-substrate	0.6359
CYP450 1A2 Inhibitor	Inhibitor	0.7040
CYP450 2C9 Inhibitor	Non-inhibitor	0.9132
CYP450 2D6 Inhibitor	Non-inhibitor	0.9424
CYP450 2C19 Inhibitor	Non-inhibitor	0.9359
CYP450 3A4 Inhibitor	Non-inhibitor	0.9015
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.8944
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9332
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.8619
AMES Toxicity	Non AMES toxic	0.9701
Carcinogens	Non-carcinogens	0.7204
Fish Toxicity	High FHMT	0.9395
Tetrahymena Pyriformis Toxicity	High TPT	0.9990
Honey Bee Toxicity	High HBT	0.6852
Biodegradation	Ready biodegradable	0.8471
Acute Oral Toxicity	IV	0.6309
Carcinogenicity (Three-class)	Non-required	0.7187

From admetSAR

Model	Value	Unit
Absorption
Aqueous solubility	-3.4754	LogS
Caco-2 Permeability	1.0021	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	1.5862	LD50, mol/kg
Fish Toxicity	1.6451	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	1.0754	pIGC50, ug/L

From admetSAR

Kingdom	Organic compounds
Superclass	Lipids and lipid-like molecules
Class	Fatty Acyls
Subclass	Fatty acids and conjugates
Intermediate Tree Nodes	Not available
Direct Parent	Long-chain fatty acids
Alternative Parents	Monocarboxylic acids and derivatives Carbonyl compounds Hydroxy fatty acids Hydrocarbon derivatives Unsaturated fatty acids Organic oxides Carboxylic acids Secondary alcohols
Molecular Framework	Aliphatic acyclic compounds
Substituents	Long-chain fatty acid - Hydroxy fatty acid - Unsaturated fatty acid - Secondary alcohol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic acyclic compound
Description	This compound 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.

From ClassyFire

General Function:: Drug binding
Specific Function:: Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered ligand binding.
Gene Name:: CNR1
Uniprot ID:: P21554
Molecular Weight:: 52857.365 Da

General Function:: Cannabinoid receptor activity
Specific Function:: Heterotrimeric G protein-coupled receptor for endocannabinoid 2-arachidonoylglycerol mediating inhibition of adenylate cyclase. May function in inflammatory response, nociceptive transmission and bone homeostasis.
Gene Name:: CNR2
Uniprot ID:: P34972
Molecular Weight:: 39680.275 Da

General Function:: Transmembrane signaling receptor activity
Specific Function:: Ligand-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular acidosis in nociceptive neurons. Involved in mediation of inflammatory pain and hyperalgesia. Sensitized by a phosphatidylinositol second messenger system activated by receptor tyrosine kinases, which involves PKC isozymes and PCL. Can be activated by endogenous compounds, including 12-hydroperoxytetraenoic acid and bradykinin. Acts as ionotropic endocannabinoid receptor with central neuromodulatory effects. Triggers a form of long-term depression (TRPV1-LTD) mediated by the endocannabinoid anandamine in the hippocampus and nucleus accumbens by affecting AMPA receptors endocytosis (By similarity). Activation by vanilloids, like capsaicin, and temperatures higher than 42 degrees Celsius, exhibits a time- and Ca(2+)-dependent outward rectification, followed by a long-lasting refractory state. Mild extracellular acidic pH (6.5) potentiates channel activation by noxious heat and vanilloids, whereas acidic conditions (pH <6) directly activate the channel.
Gene Name:: TRPV1
Uniprot ID:: Q8NER1
Molecular Weight:: 94955.33 Da

From T3DB