Quinine monohydrochloride dihydrate

Chemical name	Quinine monohydrochloride dihydrate
CAS number	6119-47-7
Flavouring type	substances
FL No.	14.155
Mixture	No
Purity of the named substance at least 95% unless otherwise specified
Reference body	EFSA

From webgate.ec.europa.eu

2D Structure
CID	16211283
IUPAC Name	(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;dihydrate;hydrochloride
InChI	InChI=1S/C20H24N2O2.ClH.2H2O/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;;;/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;1H;2*1H2/t13-,14-,19-,20+;;;/m0.../s1
InChI Key	MPQKYZPYCSTMEI-FLZPLBAKSA-N
Canonical SMILES	COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O.O.O.Cl
Molecular Formula	C20H29ClN2O4
Wikipedia	quinine hydrochloride

From Pubchem

Property Name	Property Value
Molecular Weight	396.912
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Complexity	457.0
CACTVS Substructure Key Fingerprint	A A A D c e B 7 O A A E A A A A A A A A A A A A A A A A A A A A A A A 8 W L F i A A A A A A C x 8 A A A H g A A C A A A D T z h n g Y + x v M I F g C g A z R n R A C C i C A x I i A I 2 C A + b J g O N u L E s Z u E c C h k w B H Y + A e w 4 P w O g E A B A A A C A A A A g A I A A A Q A A A A A A A A A A A = =
Topological Polar Surface Area	47.6
Monoisotopic Mass	396.182
Exact Mass	396.182
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	27
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Isotope Atom Count	0
Covalently-Bonded Unit Count	4

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.6064
Human Intestinal Absorption	HIA+	0.9758
Caco-2 Permeability	Caco2+	0.7217
P-glycoprotein Substrate	Substrate	0.8338
P-glycoprotein Inhibitor	Non-inhibitor	0.5773
P-glycoprotein Inhibitor	Inhibitor	0.6933
Renal Organic Cation Transporter	Inhibitor	0.6424
Distribution
Subcellular localization	Mitochondria	0.7111
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.7710
CYP450 2D6 Substrate	Non-substrate	0.8615
CYP450 3A4 Substrate	Substrate	0.6147
CYP450 1A2 Inhibitor	Non-inhibitor	0.7741
CYP450 2C9 Inhibitor	Non-inhibitor	0.8909
CYP450 2D6 Inhibitor	Inhibitor	0.5984
CYP450 2C19 Inhibitor	Non-inhibitor	0.7347
CYP450 3A4 Inhibitor	Non-inhibitor	0.7235
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.6790
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.5574
Human Ether-a-go-go-Related Gene Inhibition	Inhibitor	0.5542
AMES Toxicity	Non AMES toxic	0.8235
Carcinogens	Non-carcinogens	0.9592
Fish Toxicity	High FHMT	0.8116
Tetrahymena Pyriformis Toxicity	High TPT	0.9510
Honey Bee Toxicity	Low HBT	0.6615
Biodegradation	Not ready biodegradable	1.0000
Acute Oral Toxicity	III	0.4402
Carcinogenicity (Three-class)	Non-required	0.5989

From admetSAR

ADMET Predicted Profile --- Regression

Model	Value	Unit
Absorption
Aqueous solubility	-3.3118	LogS
Caco-2 Permeability	0.6701	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	2.7926	LD50, mol/kg
Fish Toxicity	1.3803	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	0.7410	pIGC50, ug/L

From admetSAR

Kingdom	Organic compounds
Superclass	Alkaloids and derivatives
Class	Cinchona alkaloids
Subclass	Not available
Intermediate Tree Nodes	Not available
Direct Parent	Cinchona alkaloids
Alternative Parents	Organopnictogen compounds Alkyl aryl ethers Hydrochlorides Aralkylamines Trialkylamines 1,2-aminoalcohols Hydrocarbon derivatives Aromatic alcohols Organic oxides Quinuclidines Piperidines Anisoles Heteroaromatic compounds Pyridines and derivatives Secondary alcohols Azacyclic compounds
Molecular Framework	Aromatic heteropolycyclic compounds
Substituents	Cinchonan-skeleton - 4-quinolinemethanol - Quinoline - Anisole - Quinuclidine - Alkyl aryl ether - Aralkylamine - Piperidine - Pyridine - Benzenoid - Heteroaromatic compound - 1,2-aminoalcohol - Secondary alcohol - Tertiary aliphatic amine - Tertiary amine - Ether - Azacycle - Organoheterocyclic compound - Alcohol - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Organic oxide - Organopnictogen compound - Amine - Hydrochloride - Organic oxygen compound - Aromatic alcohol - Aromatic heteropolycyclic compound
Description	This compound belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.