Altertoxin I - Compound Card

Altertoxin I

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Altertoxin I

Structure
Zoomed Structure
  • Family: Pleosporaceae
  • Kingdom: Fungi
  • Class: Phenolic
    • Subclass: Ellagic Acid Derivative
Canonical Smiles O=C1C[C@H](O)C2c3c1c(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-JUJMCKSGSA-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

Showing of synonyms

  • Aly AH, Ebel R, et al. (2009). Protein kinase inhibitors from the endophytic fungus Alternaria sp. isolated from Polygonum senegalense Growing in Egypt. Planta Medica,2009,75-PE55. [View]
Pubchem: 163033303
Nmrshiftdb2: 80005790
CPRiL: 160421
Structure

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

Level: 0

Mol. Weight: 288.35 g/mol

No bioactivities available.

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
-0.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.8
Plasma Protein Binding
78.21
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
10.58
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.03
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
3.94
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
-5.02
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
478.62
Hydration Free Energy
-11.0
Log(D) at pH=7.4
1.84
Log(P)
1.65
Log S
-4.0
Log(Vapor Pressure)
-9.79
Melting Point
265.69
pKa Acid
6.66
pKa Basic
3.84
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 0.9131
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9131
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8260
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8260
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8018
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8018
Renin P00797 RENI_HUMAN Homo sapiens 3 0.8007
Renin P00797 RENI_HUMAN Homo sapiens 3 0.8007
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7842
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7842
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7801
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7801
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7775
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7775
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7706
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7706
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 4 0.7597
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 4 0.7597
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7557
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7557
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7527
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7527
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7515
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7515
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7421
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7421
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7407
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7407
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7400
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7400
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7357
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7357
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7304
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7304
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7274
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7274
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7253
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7253
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7227
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7227
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7216
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7216
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7202
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7202
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7195
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7195
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7168
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7168
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7158
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7158
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7155
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7155
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7060
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7060
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7058
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7058
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7057
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7057
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7054
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7054
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7040
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7040
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7033
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7033
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7010
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7010

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