FRCD

Common Name	Isopimpinellin(F03914)
2D Structure
Description	Isopimpinellin is found in angelica. Isopimpinellin is present in the seeds of Pastinaca sativa (parsnip) Isopimpinellin belongs to the family of Furanocoumarins. These are polycyclic aromatic compounds containing a furan ring fused to a coumarin moeity.
FRCD ID	F03914
CAS Number	482-27-9
PubChem CID	68079
Formula	C13H10O5
IUPAC Name	4,9-dimethoxyfuro[3,2-g]chromen-7-one
InChI Key	DFMAXQKDIGCMTL-UHFFFAOYSA-N
InChI	InChI=1S/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3
Canonical SMILES	COC1=C2C=COC2=C(C3=C1C=CC(=O)O3)OC
Isomeric SMILES	COC1=C2C=COC2=C(C3=C1C=CC(=O)O3)OC
Synonyms	5,8-Dimethoxypsoralene Isopimpinellin 482-27-9 5,8-Dimethoxypsoralen 4,9-Dimethoxy-furo[3,2-g]chromen-7-one 4,9-Dimethoxy-7H-furo[3,2-g]chromen-7-one 7H-Furo[3,2-g][1]benzopyran-7-one, 4,9-dimethoxy- UNII-20GCF755G6 CCRIS 4347 5,8-Dimethoxy-6,7-furanocoumarin
Classifies	Plant Toxin
Update Date	Nov 13, 2018 17:07

Kingdom	Organic compounds
Superclass	Phenylpropanoids and polyketides
Class	Coumarins and derivatives
Subclass	Furanocoumarins
Intermediate Tree Nodes	Linear furanocoumarins - Psoralens
Direct Parent	8-methoxypsoralens
Alternative Parents	Hydrocarbon derivatives Organic oxides Alkyl aryl ethers Oxacyclic compounds Anisoles Furans Heteroaromatic compounds 1-benzopyrans Lactones Pyranones and derivatives Benzofurans 5-methoxypsoralens
Molecular Framework	Aromatic heteropolycyclic compounds
Substituents	5-methoxypsoralen - 8-methoxypsoralen - 1-benzopyran - Benzopyran - Benzofuran - Anisole - Alkyl aryl ether - Pyranone - Benzenoid - Pyran - Heteroaromatic compound - Furan - Lactone - Oxacycle - Organoheterocyclic compound - Ether - Organic oxygen compound - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
Description	This compound belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group.

Property Name	Property Value
Molecular Weight	246.218
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Complexity	366
Monoisotopic Mass	246.053
Exact Mass	246.053
XLogP	1.9
Formal Charge	0
Heavy Atom Count	18
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+	0.9030
Human Intestinal Absorption	HIA+	0.9896
Caco-2 Permeability	Caco2+	0.6297
P-glycoprotein Substrate	Non-substrate	0.5520
P-glycoprotein Inhibitor	Inhibitor	0.5442
P-glycoprotein Inhibitor	Inhibitor	0.5393
Renal Organic Cation Transporter	Non-inhibitor	0.8358
Distribution
Subcellular localization	Mitochondria	0.6440
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.8247
CYP450 2D6 Substrate	Non-substrate	0.9091
CYP450 3A4 Substrate	Non-substrate	0.5773
CYP450 1A2 Inhibitor	Inhibitor	0.9237
CYP450 2C9 Inhibitor	Non-inhibitor	0.7521
CYP450 2D6 Inhibitor	Inhibitor	0.9047
CYP450 2C19 Inhibitor	Inhibitor	0.9101
CYP450 3A4 Inhibitor	Inhibitor	0.7960
CYP Inhibitory Promiscuity	High CYP Inhibitory Promiscuity	0.7534
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9676
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9569
AMES Toxicity	AMES toxic	0.7091
Carcinogens	Non-carcinogens	0.9472
Fish Toxicity	High FHMT	0.9360
Tetrahymena Pyriformis Toxicity	High TPT	0.9782
Honey Bee Toxicity	High HBT	0.8451
Biodegradation	Not ready biodegradable	0.7842
Acute Oral Toxicity	III	0.5132
Carcinogenicity (Three-class)	Warning	0.4385

Model	Value	Unit
Absorption
Aqueous solubility	-3.4826	LogS
Caco-2 Permeability	0.9229	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	2.6989	LD50, mol/kg
Fish Toxicity	-0.1607	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	0.5661	pIGC50, ug/L

Title	Journal	Date	Pubmed ID
Larvicidal activity of Cnidium monnieri fruit coumarins and structurally related compounds against insecticide-susceptible and insecticide-resistant Culex pipiens pallens and Aedes aegypti.	Pest Manag Sci	2012 Jul	22389164

Targets

General Function:: Vitamin d3 25-hydroxylase activity
Specific Function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular Weight:: 57342.67 Da

Girennavar B, Jayaprakasha GK, Patil BS: Potent inhibition of human cytochrome P450 3A4, 2D6, and 2C9 isoenzymes by grapefruit juice and its furocoumarins. J Food Sci. 2007 Oct;72(8):C417-21. [17995595 ]

General Function:: Steroid hydroxylase activity
Specific Function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular Weight:: 55627.365 Da

Girennavar B, Jayaprakasha GK, Patil BS: Potent inhibition of human cytochrome P450 3A4, 2D6, and 2C9 isoenzymes by grapefruit juice and its furocoumarins. J Food Sci. 2007 Oct;72(8):C417-21. [17995595 ]