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Dihydroaltersolanol C
- Family: Fungi - Pleosporaceae
- Kingdom: Fungi
-
Class: Anthraquinone
- Subclass: Tetrahydroanthraquinone
| Canonical Smiles | COc1cc(O)c2c(c1)C(=O)[C@@H]1[C@@H](C2=O)C[C@H]([C@@]([C@@H]1O)(C)O)O |
|---|---|
| InChI | InChI=1S/C16H18O7/c1-16(22)10(18)5-8-12(15(16)21)14(20)7-3-6(23-2)4-9(17)11(7)13(8)19/h3-4,8,10,12,15,17-18,21-22H,5H2,1-2H3/t8-,10+,12-,15+,16+/m0/s1 |
| InChIKey | WUYKSAOSAAJMEW-VFGZDCLOSA-N |
| Formula | C16H18O7 |
| HBA | 7 |
| HBD | 4 |
| MW | 322.31 |
| Rotatable Bonds | 1 |
| TPSA | 124.29 |
| LogP | -0.11 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 322.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Stemphylium globuliferum | Pleosporaceae | Fungi | 245170 |
Showing of synonyms
Dihydroaltersolanol C
(2R,3R,4R,4aR,9aS)-2,3,4,8-tetrahydroxy-6-methoxy-3-methyl-2,4,4a,9a-tetrahydro-1H-anthracene-9,10-dione
CHEMBL4445979
CHEBI:202304
- Moussa M, Ebrahim W, et al. (2016). Tetrahydroanthraquinone derivatives from the mangrove-derived endophytic fungus Stemphylium globuliferum.. Tetrahedron Letters, 2016, 57(36), 4074–4078.. [View]
CPRiL:
449590
SMILES: c1cccc(c12)C(=O)C3C(C2=O)CCCC3
Level: 0
Mol. Weight: 322.31 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -5.31
- 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
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.8
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.670
- Plasma Protein Binding
- 60.74
- 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
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-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
- 5.730
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.970
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.760
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.250
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Toxic
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 0.980
- Rat (Acute)
- 3.450
- Rat (Chronic Oral)
- 3.240
- Fathead Minnow
- 4.040
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 430.120
- Hydration Free Energy
- -13.510
- Log(D) at pH=7.4
- 0.570
- Log(P)
- 0.23
- Log S
- -2.67
- Log(Vapor Pressure)
- -8.22
- Melting Point
- 198.42
- pKa Acid
- 4.93
- pKa Basic
- 5.49
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.9252 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9132 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8817 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8782 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.8708 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8634 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8627 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8508 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.8178 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 4 | 0.8155 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8046 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7862 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7551 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7465 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7417 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 3 | 0.7338 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.7315 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7294 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 3 | 0.7290 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7287 |
| GMP synthase [glutamine-hydrolyzing] | Q8IJR9 | Q8IJR9_PLAF7 | Plasmodium falciparum | 4 | 0.7222 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7169 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7163 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7106 |