1-(2,4-DIHYDROXYPHENYL)-3-(3-HYDROXY-4-METHOXYPHENYL)PROPAN-1-ONE

Chemical Names:	1-(2,4-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
CAS number:	50297-39-7
JECFA number:	2209
FEMA number:	4764
Functional Class:	Flavouring Agent FLAVOURING_AGENT

From apps.who.int

Evaluation year:	2014
ADI:	No safety concern at current levels of intake when used as a flavouring agent
Meeting:	79
Specs Code:	N
Report:	TRS 990-JECFA 79/80
Specification:	FAO JECFA Monographs 16/73

2D Structure
CID	21540063
IUPAC Name	1-(2,4-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
InChI	InChI=1S/C16H16O5/c1-21-16-7-3-10(8-15(16)20)2-6-13(18)12-5-4-11(17)9-14(12)19/h3-5,7-9,17,19-20H,2,6H2,1H3
InChI Key	GCOFCBCRRXZXNC-UHFFFAOYSA-N
Canonical SMILES	COC1=C(C=C(C=C1)CCC(=O)C2=C(C=C(C=C2)O)O)O
Molecular Formula	C16H16O5

From Pubchem

Property Name	Property Value
Molecular Weight	288.299
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Complexity	346.0
CACTVS Substructure Key Fingerprint	A A A D c e B 4 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 Y A A A A A A A A A A B Q A A A G g A A C A A A D A S A m A I y B o A A B g C I A q B S A A A C C A A k I A A I i A E G i M g N J z a G N R q A c W M l 4 B U L u Y e I 7 P T O I A A B C A A I Q A B A A A I Q A B C A A A A A A A A A A A = =
Topological Polar Surface Area	87.0
Monoisotopic Mass	288.1
Exact Mass	288.1
XLogP3	None
XLogP3-AA	3.0
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	21
Defined Atom Stereocenter Count	0
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+	0.5344
Human Intestinal Absorption	HIA+	0.7994
Caco-2 Permeability	Caco2+	0.7984
P-glycoprotein Substrate	Substrate	0.5728
P-glycoprotein Inhibitor	Non-inhibitor	0.7749
P-glycoprotein Inhibitor	Inhibitor	0.6490
Renal Organic Cation Transporter	Non-inhibitor	0.7851
Distribution
Subcellular localization	Mitochondria	0.8587
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.6715
CYP450 2D6 Substrate	Non-substrate	0.8546
CYP450 3A4 Substrate	Substrate	0.5290
CYP450 1A2 Inhibitor	Inhibitor	0.9169
CYP450 2C9 Inhibitor	Inhibitor	0.8355
CYP450 2D6 Inhibitor	Non-inhibitor	0.7061
CYP450 2C19 Inhibitor	Inhibitor	0.8850
CYP450 3A4 Inhibitor	Inhibitor	0.5459
CYP Inhibitory Promiscuity	High CYP Inhibitory Promiscuity	0.7144
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9095
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.7973
AMES Toxicity	Non AMES toxic	0.7690
Carcinogens	Non-carcinogens	0.9286
Fish Toxicity	High FHMT	0.7846
Tetrahymena Pyriformis Toxicity	High TPT	0.9972
Honey Bee Toxicity	High HBT	0.6436
Biodegradation	Not ready biodegradable	0.7021
Acute Oral Toxicity	III	0.7709
Carcinogenicity (Three-class)	Non-required	0.7110

From admetSAR

ADMET Predicted Profile --- Regression

Model	Value	Unit
Absorption
Aqueous solubility	-2.5584	LogS
Caco-2 Permeability	0.8860	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	2.1439	LD50, mol/kg
Fish Toxicity	0.5223	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	1.3911	pIGC50, ug/L

From admetSAR

Kingdom	Organic compounds
Superclass	Phenylpropanoids and polyketides
Class	Linear 1,3-diarylpropanoids
Subclass	Chalcones and dihydrochalcones
Intermediate Tree Nodes	Not available
Direct Parent	2'-Hydroxy-dihydrochalcones
Alternative Parents	Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids Alkyl-phenylketones Methoxybenzenes Organic oxides Resorcinols Aryl alkyl ketones Vinylogous acids Hydrocarbon derivatives Butyrophenones 1-hydroxy-2-unsubstituted benzenoids Cinnamylphenols Anisoles Phenoxy compounds Methoxyphenols Benzoyl derivatives
Molecular Framework	Aromatic homomonocyclic compounds
Substituents	2'-hydroxy-dihydrochalcone - Cinnamylphenol - Alkyl-phenylketone - Butyrophenone - Methoxyphenol - Phenylketone - Anisole - Benzoyl - Phenoxy compound - Phenol ether - Resorcinol - Aryl ketone - Aryl alkyl ketone - Methoxybenzene - 1-hydroxy-2-unsubstituted benzenoid - Phenol - 1-hydroxy-4-unsubstituted benzenoid - Alkyl aryl ether - Monocyclic benzene moiety - Benzenoid - Vinylogous acid - Ketone - Ether - Organic oxide - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
Description	This compound belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position.