4-Hydroxy-3,5-dimethoxycinnamic acid (mixture of isomers)

Chemical name	4-Hydroxy-3,5-dimethoxycinnamic acid (mixture of isomers)
CAS number	530-59-6
Flavouring type	substances
FL No.	08.088
Mixture	No
Purity of the named substance at least 95% unless otherwise specified
Reference body	EFSA

From webgate.ec.europa.eu

2D Structure
CID	637775
IUPAC Name	(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
InChI	InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+
InChI Key	PCMORTLOPMLEFB-ONEGZZNKSA-N
Canonical SMILES	COC1=CC(=CC(=C1O)OC)C=CC(=O)O
Molecular Formula	C11H12O5
Wikipedia	(E)-sinapic acid

From Pubchem

Property Name	Property Value
Molecular Weight	224.212
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Complexity	249.0
CACTVS Substructure Key Fingerprint	A A A D c c B w O 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 A m A I y D o A A B g C I A i D S C A A C C A A g I A A I i A A G i M g N J y K G M R q A c C M l w B U L u Y e A 4 B w O I A A B C A A A Q A B A A A I Q A A C A A A A A A A A A A A = =
Topological Polar Surface Area	76.0
Monoisotopic Mass	224.068
Exact Mass	224.068
XLogP3	None
XLogP3-AA	1.5
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	16
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+	0.5785
Human Intestinal Absorption	HIA+	0.9578
Caco-2 Permeability	Caco2+	0.7324
P-glycoprotein Substrate	Non-substrate	0.5655
P-glycoprotein Inhibitor	Non-inhibitor	0.8730
P-glycoprotein Inhibitor	Non-inhibitor	0.8588
Renal Organic Cation Transporter	Non-inhibitor	0.9159
Distribution
Subcellular localization	Mitochondria	0.8118
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.7999
CYP450 2D6 Substrate	Non-substrate	0.8919
CYP450 3A4 Substrate	Non-substrate	0.6052
CYP450 1A2 Inhibitor	Non-inhibitor	0.8445
CYP450 2C9 Inhibitor	Non-inhibitor	0.8380
CYP450 2D6 Inhibitor	Non-inhibitor	0.9297
CYP450 2C19 Inhibitor	Non-inhibitor	0.7182
CYP450 3A4 Inhibitor	Non-inhibitor	0.8748
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.7608
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9815
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9688
AMES Toxicity	Non AMES toxic	0.9023
Carcinogens	Non-carcinogens	0.8848
Fish Toxicity	High FHMT	0.9388
Tetrahymena Pyriformis Toxicity	High TPT	0.9804
Honey Bee Toxicity	High HBT	0.7902
Biodegradation	Ready biodegradable	0.5854
Acute Oral Toxicity	III	0.4500
Carcinogenicity (Three-class)	Non-required	0.6699

From admetSAR

ADMET Predicted Profile --- Regression

Model	Value	Unit
Absorption
Aqueous solubility	-2.5763	LogS
Caco-2 Permeability	0.8099	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	2.2035	LD50, mol/kg
Fish Toxicity	1.1446	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	1.1128	pIGC50, ug/L

From admetSAR

Kingdom	Organic compounds
Superclass	Phenylpropanoids and polyketides
Class	Cinnamic acids and derivatives
Subclass	Hydroxycinnamic acids and derivatives
Intermediate Tree Nodes	Not available
Direct Parent	Hydroxycinnamic acids
Alternative Parents	Coumaric acids and derivatives Alkyl aryl ethers Cinnamic acids Dimethoxybenzenes Styrenes Monocarboxylic acids and derivatives Carbonyl compounds Hydrocarbon derivatives Organic oxides Anisoles Phenoxy compounds Methoxyphenols Carboxylic acids
Molecular Framework	Aromatic homomonocyclic compounds
Substituents	Cinnamic acid - Coumaric acid or derivatives - Hydroxycinnamic acid - M-dimethoxybenzene - Dimethoxybenzene - Methoxyphenol - Phenoxy compound - Anisole - Methoxybenzene - Styrene - Phenol ether - Alkyl aryl ether - Phenol - Monocyclic benzene moiety - Benzenoid - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Ether - Organic oxygen compound - Carbonyl group - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
Description	This compound belongs to the class of organic compounds known as hydroxycinnamic acids. These are compounds containing an cinnamic acid where the benzene ring is hydroxylated.