4-Hydroxy-3-methoxycinnamaldehyde (mixture of isomers)

Chemical name	4-Hydroxy-3-methoxycinnamaldehyde (mixture of isomers)
CAS number	458-36-6
COE number	10342
Flavouring type	substances
FL No.	05.155
Mixture	No
Purity of the named substance at least 95% unless otherwise specified
Reference body	EFSA

From webgate.ec.europa.eu

2D Structure
CID	5280536
IUPAC Name	(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enal
InChI	InChI=1S/C10H10O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-7,12H,1H3/b3-2+
InChI Key	DKZBBWMURDFHNE-NSCUHMNNSA-N
Canonical SMILES	COC1=C(C=CC(=C1)C=CC=O)O
Molecular Formula	C10H10O3
Wikipedia	Coniferyl aldehyde

From Pubchem

Property Name	Property Value
Molecular Weight	178.187
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Complexity	189.0
CACTVS Substructure Key Fingerprint	A A A D c c B w 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 A A A A A A A A A A A B A A A A G g A A C A A A D A S g m A I y B o A A B g C I A i h S g A A C C A A g I A A I i A A G i M g N J i K G M R q A c C M k w B E L u Y e A w B A O I A A B A A A A Q A B A A A I A A A C A A A A A A A A A A A = =
Topological Polar Surface Area	46.5
Monoisotopic Mass	178.063
Exact Mass	178.063
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	13
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Isotope Atom Count	0
Covalently-Bonded Unit Count	1

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.7267
Human Intestinal Absorption	HIA+	1.0000
Caco-2 Permeability	Caco2+	0.9028
P-glycoprotein Substrate	Non-substrate	0.6266
P-glycoprotein Inhibitor	Non-inhibitor	0.7664
P-glycoprotein Inhibitor	Non-inhibitor	0.8207
Renal Organic Cation Transporter	Non-inhibitor	0.8845
Distribution
Subcellular localization	Mitochondria	0.8786
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.7170
CYP450 2D6 Substrate	Non-substrate	0.8628
CYP450 3A4 Substrate	Non-substrate	0.6367
CYP450 1A2 Inhibitor	Non-inhibitor	0.5464
CYP450 2C9 Inhibitor	Non-inhibitor	0.9114
CYP450 2D6 Inhibitor	Non-inhibitor	0.9505
CYP450 2C19 Inhibitor	Non-inhibitor	0.6187
CYP450 3A4 Inhibitor	Non-inhibitor	0.8912
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.6990
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9563
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9493
AMES Toxicity	Non AMES toxic	0.8416
Carcinogens	Non-carcinogens	0.8793
Fish Toxicity	High FHMT	0.8871
Tetrahymena Pyriformis Toxicity	High TPT	0.9855
Honey Bee Toxicity	High HBT	0.7982
Biodegradation	Ready biodegradable	0.6152
Acute Oral Toxicity	III	0.7861
Carcinogenicity (Three-class)	Non-required	0.5356

From admetSAR

ADMET Predicted Profile --- Regression

Model	Value	Unit
Absorption
Aqueous solubility	-1.8754	LogS
Caco-2 Permeability	1.4048	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	1.6374	LD50, mol/kg
Fish Toxicity	1.2454	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	0.7626	pIGC50, ug/L

From admetSAR

Kingdom	Organic compounds
Superclass	Benzenoids
Class	Phenols
Subclass	Methoxyphenols
Intermediate Tree Nodes	Not available
Direct Parent	Methoxyphenols
Alternative Parents	Aldehydes Alkyl aryl ethers Styrenes Methoxybenzenes Organic oxides Enals Hydrocarbon derivatives Cinnamaldehydes 1-hydroxy-2-unsubstituted benzenoids Anisoles Phenoxy compounds
Molecular Framework	Aromatic homomonocyclic compounds
Substituents	Cinnamaldehyde - Methoxyphenol - Phenoxy compound - Anisole - Methoxybenzene - Styrene - Phenol ether - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Monocyclic benzene moiety - Enal - Alpha,beta-unsaturated aldehyde - Ether - Hydrocarbon derivative - Carbonyl group - Aldehyde - Organic oxide - Organic oxygen compound - Organooxygen compound - Aromatic homomonocyclic compound
Description	This compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.