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Altersolanol A
- Family: Fungi - Pleosporaceae
- Kingdom: Fungi
- Class: Polyketide
| Canonical Smiles | COc1cc(O)c2c(c1)C(=O)C1=C(C2=O)[C@H](O)[C@H]([C@@]([C@@H]1O)(C)O)O |
|---|---|
| InChI | InChI=1S/C16H16O8/c1-16(23)14(21)10-9(13(20)15(16)22)12(19)8-6(11(10)18)3-5(24-2)4-7(8)17/h3-4,13-15,17,20-23H,1-2H3/t13-,14+,15+,16-/m0/s1 |
| InChIKey | VSMBLBOUQJNJIL-JJXSEGSLSA-N |
| Formula | C16H16O8 |
| HBA | 8 |
| HBD | 5 |
| MW | 336.3 |
| Rotatable Bonds | 1 |
| TPSA | 144.52 |
| LogP | -1.08 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.38 |
| Exact Mass | 336.08 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ampelomyces species | Phaeosphaeriaceae | Fungi | 50729 |
| 2 | Stemphylium globuliferum | Pleosporaceae | Fungi | 245170 |
Showing of synonyms
Altersolanol A
22268-16-2
As-A 2
(1S,2R,3S,4R)-1,2,3,4,8-pentahydroxy-6-methoxy-3-methyl-2,4-dihydro-1H-anthracene-9,10-dione
NSC 173943
DTXSID10891800
9,10-Anthracenedione, 1,2,3,4-tetrahydro-1,2,3,4,5-pentahydroxy-7-methoxy-2-methyl-, (1R-(1alpha,2beta,3beta,4alpha))-
DTXCID101031037
CHEBI:2615
ZS3LU23BE3
Stemphylin
AC1L3IB0
AC1Q6I5J
NSC-173943
UNII-ZS3LU23BE3
CHEMBL512054
SCHEMBL2793105
DTXSID701043575
BDBM50480485
HB3756
HY-125461
CS-0091695
NS00094875
Q27105737
(1R,2S,3R,4S)-1,2,3,4-Tetrahydro-1,2,3,4,5-pentahydroxy-7-methoxy-2-methyl-9,10-anthracenedione
(1R-(1alpha,2beta,3beta,4alpha))-1,2,3,4-Tetrahydro-1,2,3,4,5-pentahydroxy-7-methoxy-2-methyl-9,10-anthracenedione
116948-40-4
9,10-Anthracenedione, 1,2,3,4-tetrahydro-1,2,3,4,5-pentahydroxy-7-methoxy-2-methyl-, (1R,2S,3R,4S)-
Rel-(1R,2S,3R,4S)-1,2,3,4-Tetrahydro-1,2,3,4,5- pentahydroxy-7-methoxy-2-methyl-9,10-anthracenedione
- Teiten MH, Mack F, et al. (2013). Anticancer effect of altersolanol A, a metabolite produced by the endophytic fungus Stemphylium globuliferum, mediated by its pro-apoptotic and anti-invasive potential via the inhibition of NF-κB activity. Bioorganic and Medicinal Chemistry,2013,21(13),3850-3858. [View] [PubMed]
- Aly AH, Edrada-Ebel R, et al. (2008). Bioactive metabolites from the endophytic fungus Ampelomyces sp. isolated from the medicinal plant Urospermum picroides. Phytochemistry,2008,69(8),1716-1725. [View] [PubMed]
Pubchem:
89644
Cas:
22268-16-2
Gnps:
CCMSLIB00005727194
Kegg Ligand:
C10296
Chebi:
2615
Nmrshiftdb2:
70000557
Chembl:
CHEMBL512054
Comptox:
DTXSID10891800
Bindingdb:
50480485
CPRiL:
156663
SMILES: c1cccc(c12)C(=O)C3=C(C2=O)CCCC3
Level: 0
Mol. Weight: 336.3 g/mol
Anticancer
Antimicrobial
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -5.73
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.080
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -0.88
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.630
- Plasma Protein Binding
- 67.6
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.000
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.540
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.920
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.670
- 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
- 0.220
- Rat (Acute)
- 2.540
- Rat (Chronic Oral)
- 4.020
- Fathead Minnow
- 4.000
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 471.070
- Hydration Free Energy
- -14.660
- Log(D) at pH=7.4
- 0.330
- Log(P)
- 0.39
- Log S
- -2.95
- Log(Vapor Pressure)
- -9.9
- Melting Point
- 200.68
- pKa Acid
- 4.04
- pKa Basic
- 6.29
| 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 | 0.9279 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.9279 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9055 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9055 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8672 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8672 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8639 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8639 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8392 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8392 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8335 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8335 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8283 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8283 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.8083 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.8083 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7977 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7977 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7920 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7920 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7591 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7591 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 4 | 0.7479 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 4 | 0.7479 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.7439 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.7439 |
| Metallophosphoesterase MPPED2 | B1WBP0 | MPPD2_RAT | Rattus norvegicus | 4 | 0.7399 |
| Metallophosphoesterase MPPED2 | B1WBP0 | MPPD2_RAT | Rattus norvegicus | 4 | 0.7399 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.7365 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.7365 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7358 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7358 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7351 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7351 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7308 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7308 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7267 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7267 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7244 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7244 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7221 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7221 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7205 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7205 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 3 | 0.7143 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 3 | 0.7143 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7129 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7129 |
| GMP synthase [glutamine-hydrolyzing] | Q8IJR9 | Q8IJR9_PLAF7 | Plasmodium falciparum | 4 | 0.7036 |
| GMP synthase [glutamine-hydrolyzing] | Q8IJR9 | Q8IJR9_PLAF7 | Plasmodium falciparum | 4 | 0.7036 |
| Glucose-1-phosphate thymidylyltransferase | Q9AGY4 | Q9AGY4_ANETH | Aneurinibacillus thermoaerophilus | 4 | 0.7022 |
| Glucose-1-phosphate thymidylyltransferase | Q9AGY4 | Q9AGY4_ANETH | Aneurinibacillus thermoaerophilus | 4 | 0.7022 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 4 | 0.7017 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 4 | 0.7017 |