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Integrastatin B
- Family: Fungi - Didymellaceae
- Kingdom: Fungi
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | COc1cc2c(c(c1O)O)C1(C)Oc3c(C(C2=O)(O1)C)c(C=O)cc(c3O)OC |
|---|---|
| InChI | InChI=1S/C20H18O9/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/h5-7,22-24H,1-4H3 |
| InChIKey | PECRJLBPKXQZDC-UHFFFAOYSA-N |
| Formula | C20H18O9 |
| HBA | 9 |
| HBD | 3 |
| MW | 402.36 |
| Rotatable Bonds | 3 |
| TPSA | 131.75 |
| LogP | 2.33 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.3 |
| Exact Mass | 402.1 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Epicoccum sp. | Didymellaceae | Fungi | 1859956 |
Showing of synonyms
Integrastatin B
324518-09-4
4,7,8-trihydroxy-3,9-dimethoxy-6,12-dimethyl-11-oxo-11,12-dihydro-6H-6,12-epoxydibenzo[b,f]oxocine-1-carbaldehyde
6,12-Epoxy-6H-dibenz(b,f)oxocin-1-carboxaldehyde, 11,12-dihydro-4,7,8-trihydroxy-3,9-dimethoxy-6,12-dimethyl-11-oxo-
6,12-Epoxy-6H-dibenz[b,f]oxocin-1-carboxaldehyde, 11,12-dihydro-4,7,8-trihydroxy-3,9-dimethoxy-6,12-dimethyl-11-oxo-
Trihydroxy-dimethoxy-dimethyl-oxo-[?]carbaldehyde
CHEBI:66080
DTXSID50954206
Q27134593
6,11,12-trihydroxy-5,13-dimethoxy-1,9-dimethyl-16-oxo-8,17-dioxatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10,12,14-hexaene-3-carbaldehyde
Rac-4,7,8-trihydroxy-3,9-dimethoxy-6,12-dimethyl-11-oxo-11,12-dihydro-6H-6,12-epoxydibenzo[b,f]oxocine-1-carbaldehyde
- 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]
No compound-protein relationship available.
SMILES: c1cccc(c12)C3Oc4c(C(O3)C2=O)cccc4
Level: 0
Mol. Weight: 402.36 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.96
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.820
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.29
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.850
- Plasma Protein Binding
- 40.63
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-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
- 14.470
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.530
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.870
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 7.880
- 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
- Toxic
- T. Pyriformis
- -9.140
- Rat (Acute)
- 2.430
- Rat (Chronic Oral)
- 2.590
- Fathead Minnow
- 4.590
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 471.240
- Hydration Free Energy
- -7.950
- Log(D) at pH=7.4
- 1.490
- Log(P)
- 1.18
- Log S
- -4.31
- Log(Vapor Pressure)
- -7.81
- Melting Point
- 237.08
- pKa Acid
- 5.93
- pKa Basic
- 2.04
| 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 | 0.8655 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8537 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8344 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8199 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 5 | 0.8111 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7437 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7434 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7348 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7178 |
| Flavin reductase like domain-containing protein | Q4UKE8 | Q4UKE8_RICFE | Rickettsia felis | 3 | 0.7154 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7105 |