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Altertoxin I

Family: Fungi - Pleosporaceae
Kingdom: Fungi
Class: Coumarin
- Subclass: Coumestan

Canonical Smiles	O=C1C[C@H](O)[C@@H]2c3c1c(O)ccc3c1c3[C@@]2(O)CCC(=O)c3c(cc1)O
InChI	InChI=1S/C20H16O6/c21-10-3-1-8-9-2-4-11(22)17-12(23)5-6-20(26,18(9)17)19-14(25)7-13(24)16(10)15(8)19/h1-4,14,19,21-22,25-26H,5-7H2/t14-,19+,20-/m0/s1
InChIKey	GJIALGLHOBXNAT-KPOBHBOGSA-N
Formula	C₂₀H₁₆O₆
HBA	6
HBD	4
MW	352.34
Rotatable Bonds	0
TPSA	115.06
LogP	1.97
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	352.09
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Alternaria species	Pleosporaceae	Fungi	5598
2	Alternaria species	Pleosporineae	Fungi	5598

Showing of synonyms

Aly AH, Edrada-Ebel R, et al. (2008). Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense. Journal of Natural Products,2008,71(6),972-980. [View] [PubMed]

Pubchem: 104860

Cas: 56258-32-3

Gnps: CCMSLIB00000081750

Zinc: ZINC000006092274

Nmrshiftdb2: 70003530

Chembl: CHEMBL521470

Bindingdb: 50479261

CPRiL: 160421

SMILES: c12c3c4c(ccc3)C(=O)CCC4C5c1c(C(=O)CC5)ccc2

Level: 0

Mol. Weight: 352.34 g/mol

Cytotoxic

Kinase inhibitory

Absorption

Caco-2 (logPapp): -5.74
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.94
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.91

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.8
Plasma Protein Binding: 83.26
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 10.57
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.13
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.58
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 3.95
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -4.05
Rat (Acute): 2.8
Rat (Chronic Oral): 3.39
Fathead Minnow: 4.07
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 480.49
Hydration Free Energy: -10.97
Log(D) at pH=7.4: 1.83
Log(P): 1.64
Log S: -4.05
Log(Vapor Pressure): -9.98
Melting Point: 275.02
pKa Acid: 6.65
pKa Basic: 3.8

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9634
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9634
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9629
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9629
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8195
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8195
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8067
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8067
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7941
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7941
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7935
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7935
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7828
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7828
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7509
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7509
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7489
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7489
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7466
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7466
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7421
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7421
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7340
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7340
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7334
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7334
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7288
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7288
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7286
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7286
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	3	0.7211
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	3	0.7211
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7132
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7132
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7096
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7096
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7006
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7006

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