(1R,2S,5R)-Menthyl salicylate

Chemical name	(1R,2S,5R)-Menthyl salicylate
CAS number	89-46-3
Flavouring type	substances
FL No.	09.621
Mixture	No
Purity of the named substance at least 95% unless otherwise specified
Reference body	EFSA

From webgate.ec.europa.eu

2D Structure
CID	20055232
IUPAC Name	[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2-hydroxybenzoate
InChI	InChI=1S/C17H24O3/c1-11(2)13-9-8-12(3)10-16(13)20-17(19)14-6-4-5-7-15(14)18/h4-7,11-13,16,18H,8-10H2,1-3H3/t12-,13+,16-/m1/s1
InChI Key	SJOXEWUZWQYCGL-DVOMOZLQSA-N
Canonical SMILES	CC1CCC(C(C1)OC(=O)C2=CC=CC=C2O)C(C)C
Molecular Formula	C17H24O3
Wikipedia	(+/-)-menthyl salicylate

From Pubchem

Property Name	Property Value
Molecular Weight	276.376
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Complexity	326.0
CACTVS Substructure Key Fingerprint	A A A D c e 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 w Y A A A A A A A A A A B A A A A G g A A C A A A D R S g m A I y D o A A B g C I A i D S C A A C A A A k I A A I i A E G C M g I J z a C N R q C c U A l 4 B E I u Y e I y P C O g A A A A A A I A A C A A A I A A B A A A A A A A A A A A A = =
Topological Polar Surface Area	46.5
Monoisotopic Mass	276.173
Exact Mass	276.173
XLogP3	None
XLogP3-AA	5.4
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	20
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Isotope Atom Count	0
Covalently-Bonded Unit Count	1

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.8603
Human Intestinal Absorption	HIA+	0.9945
Caco-2 Permeability	Caco2+	0.8235
P-glycoprotein Substrate	Substrate	0.5351
P-glycoprotein Inhibitor	Non-inhibitor	0.7292
P-glycoprotein Inhibitor	Non-inhibitor	0.7639
Renal Organic Cation Transporter	Non-inhibitor	0.8160
Distribution
Subcellular localization	Mitochondria	0.8931
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.7422
CYP450 2D6 Substrate	Non-substrate	0.8273
CYP450 3A4 Substrate	Substrate	0.6168
CYP450 1A2 Inhibitor	Inhibitor	0.6917
CYP450 2C9 Inhibitor	Inhibitor	0.5766
CYP450 2D6 Inhibitor	Non-inhibitor	0.9300
CYP450 2C19 Inhibitor	Inhibitor	0.6194
CYP450 3A4 Inhibitor	Non-inhibitor	0.8350
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.8927
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9155
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.7076
AMES Toxicity	Non AMES toxic	0.8881
Carcinogens	Non-carcinogens	0.8132
Fish Toxicity	High FHMT	0.9969
Tetrahymena Pyriformis Toxicity	High TPT	0.9957
Honey Bee Toxicity	High HBT	0.7417
Biodegradation	Not ready biodegradable	0.8664
Acute Oral Toxicity	III	0.6115
Carcinogenicity (Three-class)	Non-required	0.6654

From admetSAR

ADMET Predicted Profile --- Regression

Model	Value	Unit
Absorption
Aqueous solubility	-5.5278	LogS
Caco-2 Permeability	1.3161	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	1.9558	LD50, mol/kg
Fish Toxicity	-0.2912	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	2.5131	pIGC50, ug/L

From admetSAR

Kingdom	Organic compounds
Superclass	Benzenoids
Class	Benzene and substituted derivatives
Subclass	Benzoic acids and derivatives
Intermediate Tree Nodes	Benzoic acid esters
Direct Parent	o-Hydroxybenzoic acid esters
Alternative Parents	Carboxylic acid esters 1-hydroxy-4-unsubstituted benzenoids Salicylic acid and derivatives Aromatic monoterpenoids Monocarboxylic acids and derivatives Menthane monoterpenoids Hydrocarbon derivatives 1-hydroxy-2-unsubstituted benzenoids Organooxygen compounds Benzoyl derivatives Vinylogous acids Monocyclic monoterpenoids Organic oxides
Molecular Framework	Aromatic homomonocyclic compounds
Substituents	O-hydroxybenzoic acid ester - Aromatic monoterpenoid - Monocyclic monoterpenoid - P-menthane monoterpenoid - Salicylic acid or derivatives - Monoterpenoid - Benzoyl - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Vinylogous acid - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organooxygen compound - Aromatic homomonocyclic compound
Description	This compound belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.