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Altenuene
- Family: Fungi - Pleosporaceae
- Kingdom: Fungi
-
Class: Coumarin
- Subclass: Coumestan
| Canonical Smiles | COc1cc(O)c2c(c1)C1=C[C@H](O)[C@H](C[C@@]1(OC2=O)C)O |
|---|---|
| InChI | InChI=1S/C15H16O6/c1-15-6-12(18)10(16)5-9(15)8-3-7(20-2)4-11(17)13(8)14(19)21-15/h3-5,10,12,16-18H,6H2,1-2H3/t10-,12-,15-/m0/s1 |
| InChIKey | MMHTXEATDNFMMY-WBIUFABUSA-N |
| Formula | C15H16O6 |
| HBA | 6 |
| HBD | 3 |
| MW | 292.29 |
| Rotatable Bonds | 1 |
| TPSA | 96.22 |
| LogP | 0.84 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.4 |
| Exact Mass | 292.09 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Alternaria species | Pleosporaceae | Fungi | 5598 |
| 2 | Alternaria species | Pleosporaceae | Fungi | 5598 |
| 3 | Alternaria species | Pleosporineae | Fungi | 5598 |
Showing of synonyms
Altenuene
29752-43-0
(2S,3S,4aS)-2,3,7-trihydroxy-9-methoxy-4a-methyl-3,4-dihydro-2H-benzo[c]chromen-6-one
BRN 4153870
CCRIS 8303
DTXSID60891799
5-18-05-00113 (Beilstein Handbook Reference)
6H-Dibenzo(b,d)pyran-6-one, 2,3,4,4a-tetrahydro-2,3,7-trihydroxy-9-methoxy-4a-methyl-, (2-alpha,3-beta,4a-beta)-(+-)-
CHEBI:144317
(2S,3S,4aS)-2,3,7-trihydroxy-9-methoxy-4a-methyl-3,4-dihydro-2H-benzo(c)chromen-6-one
DTXCID401031036
(2R,3R,4AR)-2,3,7-trihydroxy-9-methoxy-4a-methyl-2,3,4,4a-tetrahydro-6H-benzo(c)chromen-6-one
(2R,3R,4aR)-2,3,7-trihydroxy-9-methoxy-4a-methyl-2,3,4,4a-tetrahydro-6H-benzo[c]chromen-6-one
(2R,3R,4aR)-2,3,7-trihydroxy-9-methoxy-4a-methyl-2,3,4,4a-tetrahydro-6H-dibenzo(b,d)pyran-6-one
(2R,3R,4aR)-2,3,7-trihydroxy-9-methoxy-4a-methyl-2,3,4,4a-tetrahydro-6H-dibenzo[b,d]pyran-6-one
6H-Dibenzo[b,d]pyran-6-one, 2,3,4,4a-tetrahydro-2,3,7-trihydroxy-9-methoxy-4a-methyl-, (2.alpha.,3.beta.,4a.beta.)-(.+/-.)-
6H-Dibenzo(b,d)pyran-6-one, 2,3,4,4a-tetrahydro-2,3,7-trihydroxy-9-methoxy-4a-methyl-, (2alpha,3beta,4abeta)-(+-)-
(2r,3r,4ar)-2,3,4,4a-tetrahydro-2,3,7-trihydroxy-9-methoxy-4a-methyl-6h-dibenzo(b,d)pyran-6-one
(2r,3r,4ar)-2,3,4,4a-tetrahydro-2,3,7-trihydroxy-9-methoxy-4a-methyl-6h-dibenzo[b,d]pyran-6-one
Mmhtxeatdnfmmy-uhfffaoysa-n
CHEMBL482228
MEGxm0_000136
ACon0_001041
ACon1_002175
MSK001410
MSK001410-100M
NCGC00179755-01
NCGC00179755-02
DA-70735
Altenuene Solution in Methanol, 100ug/mL
NS00094874
BRD-K26184114-001-01-8
Q63409701
- Aly AH, Edrada-Ebel R, et al. (2008). Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense. Journal of Natural Products,2008,71(6),972-980. [View] [PubMed]
- 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:
34687
Cas:
29752-43-0
Gnps:
CCMSLIB00006406961
Zinc:
ZINC000004533847
Nmrshiftdb2:
80003245
Chembl:
CHEMBL482228
Comptox:
DTXSID60891799
CPRiL:
208333
SMILES: c1cccc(c12)C(=O)OC3C2=CCCC3
Level: 0
Mol. Weight: 292.29 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.95
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.550
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.33
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.640
- Plasma Protein Binding
- 42.98
- 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
- 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
- 9.410
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.000
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- -0.130
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.760
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 0.880
- Rat (Acute)
- 2.600
- Rat (Chronic Oral)
- 2.650
- 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
- 406.650
- Hydration Free Energy
- -12.740
- Log(D) at pH=7.4
- 1.290
- Log(P)
- 1.31
- Log S
- -2.31
- Log(Vapor Pressure)
- -7.3
- Melting Point
- 180.46
- pKa Acid
- 6.91
- pKa Basic
- 3.93
| 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 | 0.9230 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.9230 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9052 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9052 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.8850 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.8850 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8802 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8802 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8571 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8571 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8118 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8118 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7985 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7985 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7967 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7967 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7536 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7536 |
| Purine nucleoside phosphorylase DeoD-type | Q5EEL8 | DEOD_BACCE | Bacillus cereus | 3 | 0.7492 |
| Purine nucleoside phosphorylase DeoD-type | Q5EEL8 | DEOD_BACCE | Bacillus cereus | 3 | 0.7492 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7437 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7437 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7329 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7329 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7317 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7317 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7284 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7284 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7262 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7262 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7262 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7262 |
| Glutathione S-transferase | Q8ILQ7 | GST_PLAFA | Plasmodium falciparum | 3 | 0.7258 |
| Glutathione S-transferase | Q8ILQ7 | GST_PLAFA | Plasmodium falciparum | 3 | 0.7258 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7215 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7215 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7193 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7193 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7149 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7149 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.7137 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.7137 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7102 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7102 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7076 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7076 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7057 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7057 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7054 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7054 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7051 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7051 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7048 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7048 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7036 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7036 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.7026 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.7026 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7025 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7025 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7022 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7022 |