Integrastatin A - Compound Card

Integrastatin A

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Integrastatin A

Structure
Zoomed Structure
  • Family: Fungi - Didymellaceae
  • Kingdom: Fungi
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles COc1cc2c(c(c1O)O)C1(C)Oc3c(C(C2=O)(O1)C)c(CO)cc(c3O)OC
InChI InChI=1S/C20H20O9/c1-19-12-8(7-21)5-10(26-3)15(23)17(12)28-20(2,29-19)13-9(18(19)25)6-11(27-4)14(22)16(13)24/h5-6,21-24H,7H2,1-4H3
InChIKey LNYIJBSSELCSKA-UHFFFAOYSA-N
Formula C20H20O9
HBA 9
HBD 4
MW 404.37
Rotatable Bonds 3
TPSA 134.91
LogP 2.01
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 404.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Epicoccum sp. Didymellaceae Fungi 1859956

Showing of synonyms

  • Talontsi FM, Dittrich B, et al. (2013). Epicoccolides: Antimicrobial and Antifungal Polyketides from an Endophytic Fungus Epicoccum sp. Associated with Theobroma cacao. Eur. J. Org. Chem., 2013: 3174-3180. [View]
Pubchem: 456304
Chebi: 66079
Metabolights: MTBLC66079

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C3Oc4c(C(O3)C2=O)cccc4

Level: 0

Mol. Weight: 404.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.91
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.930
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.31

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.920
Plasma Protein Binding
42.3
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
15.200
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.480
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.860
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.430
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
-9.780
Rat (Acute)
2.400
Rat (Chronic Oral)
3.100
Fathead Minnow
4.450
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
482.520
Hydration Free Energy
-8.660
Log(D) at pH=7.4
1.530
Log(P)
0.57
Log S
-4.02
Log(Vapor Pressure)
-7.45
Melting Point
213.23
pKa Acid
5.99
pKa Basic
3.53
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8713
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8520
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8407
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8169
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7462
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7443
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7432
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7348
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7184
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7127
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7097

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