ORCHIL AND ORCEIN

Synonyms:	CI NATURAL RED 28, LACMUS, LITMUS
Chemical Names:	ORCEIN AND LITMUS (THE COLOURING PRINCIPLES)
CAS number:	1400-62-0 (ORCEIN)
INS:	182
Functional Class:	Food Additives COLOUR

From apps.who.int

2D Structure
CID	5386447
IUPAC Name	2,8-bis(2,4-dihydroxy-6-methylanilino)-1,9-dimethyldibenzofuran-3,7-dione
InChI	InChI=1S/C28H24N2O7/c1-11-5-15(31)7-17(33)25(11)29-27-13(3)23-21(9-19(27)35)37-22-10-20(36)28(14(4)24(22)23)30-26-12(2)6-16(32)8-18(26)34/h5-10,29-34H,1-4H3
InChI Key	VPEASJIRGSVXBF-UHFFFAOYSA-N
Canonical SMILES	CC1=CC(=CC(=C1NC2=C(C3=C4C(=C(C(=O)C=C4OC3=CC2=O)NC5=C(C=C(C=C5C)O)O)C)C)O)O
Molecular Formula	C28H24N2O7
Wikipedia	pacein

From Pubchem

Property Name	Property Value
Molecular Weight	500.507
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	4
Complexity	1100.0
CACTVS Substructure Key Fingerprint	A A A D c e B 7 O A A A A A A A A A A A A A A A A A A A A Q A A A A A w Y I E A A A A A A E A B Q A A A H g A Q C A A A D A y B m A A y x o L A B g C I A q R S Q A C C C A A h I A A A i A C H T M g K J y L S s b O G c A h l w B X Y + Q e w 4 B Q O A E A B C A A C E A A A g A I Q A A Q g A A A A A A A A A A = =
Topological Polar Surface Area	148.0
Monoisotopic Mass	500.158
Exact Mass	500.158
XLogP3	None
XLogP3-AA	2.9
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	37
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-	0.9292
Human Intestinal Absorption	HIA+	0.9427
Caco-2 Permeability	Caco2-	0.6146
P-glycoprotein Substrate	Substrate	0.6713
P-glycoprotein Inhibitor	Non-inhibitor	0.6802
P-glycoprotein Inhibitor	Non-inhibitor	0.6616
Renal Organic Cation Transporter	Non-inhibitor	0.9331
Distribution
Subcellular localization	Mitochondria	0.5630
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.6773
CYP450 2D6 Substrate	Non-substrate	0.8498
CYP450 3A4 Substrate	Substrate	0.5110
CYP450 1A2 Inhibitor	Inhibitor	0.9106
CYP450 2C9 Inhibitor	Inhibitor	0.8949
CYP450 2D6 Inhibitor	Inhibitor	0.8932
CYP450 2C19 Inhibitor	Inhibitor	0.8994
CYP450 3A4 Inhibitor	Non-inhibitor	0.8546
CYP Inhibitory Promiscuity	High CYP Inhibitory Promiscuity	0.8558
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.8580
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.8077
AMES Toxicity	Non AMES toxic	0.5815
Carcinogens	Non-carcinogens	0.8718
Fish Toxicity	High FHMT	0.9957
Tetrahymena Pyriformis Toxicity	High TPT	0.9982
Honey Bee Toxicity	High HBT	0.5331
Biodegradation	Not ready biodegradable	0.9870
Acute Oral Toxicity	III	0.5777
Carcinogenicity (Three-class)	Danger	0.4153

From admetSAR

ADMET Predicted Profile --- Regression

Model	Value	Unit
Absorption
Aqueous solubility	-3.9240	LogS
Caco-2 Permeability	0.5829	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	2.4509	LD50, mol/kg
Fish Toxicity	-0.2888	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	1.0071	pIGC50, ug/L

From admetSAR

Kingdom	Organic compounds
Superclass	Organoheterocyclic compounds
Class	Benzofurans
Subclass	Not available
Intermediate Tree Nodes	Not available
Direct Parent	Benzofurans
Alternative Parents	Organopnictogen compounds 1-hydroxy-4-unsubstituted benzenoids Aminotoluenes Organic oxides Resorcinols o-Aminophenols Hydrocarbon derivatives Enamines 1-hydroxy-2-unsubstituted benzenoids Furans Heteroaromatic compounds Aniline and substituted anilines Cyclic ketones Oxacyclic compounds Secondary alkylarylamines Meta cresols
Molecular Framework	Aromatic heteropolycyclic compounds
Substituents	Benzofuran - Resorcinol - Aniline or substituted anilines - Aminotoluene - M-cresol - Aminophenol - O-aminophenol - P-aminophenol - Toluene - 1-hydroxy-2-unsubstituted benzenoid - 1-hydroxy-4-unsubstituted benzenoid - Secondary aliphatic/aromatic amine - Phenol - Benzenoid - Monocyclic benzene moiety - Heteroaromatic compound - Furan - Ketone - Cyclic ketone - Oxacycle - Enamine - Secondary amine - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Amine - Organic oxide - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
Description	This compound belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.