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Cis-2,3-dihydro-2,3,9-trimethyl-3-(2-keto-3,4-epoxy-4-methylpentyl)-4H-furo[3,2-c][1]benzopyran-4-one

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Coumarin

Canonical Smiles	O=C([C@@H]1OC1(C)C)C[C@]1(C)[C@H](C)Oc2c1c(=O)oc1c2c(C)ccc1
InChI	InChI=1S/C20H22O5/c1-10-7-6-8-13-14(10)16-15(18(22)24-13)20(5,11(2)23-16)9-12(21)17-19(3,4)25-17/h6-8,11,17H,9H2,1-5H3/t11-,17-,20+/m0/s1
InChIKey	QMWJPFXMOOPDTD-PJFOTGOESA-N
Formula	C₂₀H₂₂O₅
HBA	5
HBD	0
MW	342.39
Rotatable Bonds	3
TPSA	69.04
LogP	3.28
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	342.15
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Vernonia brachycalyx	Asteraceae	Plantae	434693

Showing of synonyms

Oketch-Rabah HA, Lemmich E, et al. (1997). Two new antiprotozoal 5-methylcoumarins from Vernonia brachycalyx. Journal of Natural Products,1997,60(5),458-461. [View] [PubMed]

Pubchem: 44566632

Zinc: ZINC000014950836

Chembl: CHEMBL465559

No compound-protein relationship available.

SMILES: O1CC1C(=O)CC2COc(c23)c4c(oc3=O)cccc4

Level: 1

Mol. Weight: 342.39 g/mol

SMILES: C1COc(c12)c3c(oc2=O)cccc3

Level: 0

Mol. Weight: 342.39 g/mol

SMILES: C1CO1

Level: 0

Mol. Weight: 342.39 g/mol

Anti-leishmanial

Anti-plasmodial

Absorption

Caco-2 (logPapp): -4.89
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.520
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.42

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.720
Plasma Protein Binding: 70.06
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 16.110
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.610
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.020
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.090
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: 0.420
Rat (Acute): 3.920
Rat (Chronic Oral): 1.390
Fathead Minnow: 4.560
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 426.270
Hydration Free Energy: -6.940
Log(D) at pH=7.4: 2.770
Log(P): 2.82
Log S: -4.36
Log(Vapor Pressure): -7.13
Melting Point: 123.08
pKa Acid: 5.33
pKa Basic: 2.9

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.9772
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.9772
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.8494
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.8494
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.8204
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.8204
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7820
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7820
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.7730
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.7730
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7653
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7653
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7625
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7625
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7591
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7591
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7585
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7585
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7499
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7499
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7477
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7477
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7477
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7477
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7468
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7468
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7410
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7410
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7365
Odorant-binding protein	P81245	OBP_PIG	Sus scrofa	3	0.7365
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7365
Odorant-binding protein	P81245	OBP_PIG	Sus scrofa	3	0.7365
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7279
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7279
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7219
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7219
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7164
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7164
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7140
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7140
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7117
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7117
Actin, alpha skeletal muscle	P68135	ACTS_RABIT	Oryctolagus cuniculus	3	0.7104
Actin, alpha skeletal muscle	P68135	ACTS_RABIT	Oryctolagus cuniculus	3	0.7104
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	4	0.7101
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	4	0.7101
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7086
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7086
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7074
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7074
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7066
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7066
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7044
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.7044
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7044
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7044
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.7044
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7044
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7031
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7031
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7012
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7012

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