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10-methoxytetrahydroalstonine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | COc1ccc2c(c1)c1CCN3[C@H](c1[nH]2)C[C@H]1[C@@H](C3)[C@H](C)OC=C1C(=O)OC |
|---|---|
| InChI | InChI=1S/C22H26N2O4/c1-12-17-10-24-7-6-14-16-8-13(26-2)4-5-19(16)23-21(14)20(24)9-15(17)18(11-28-12)22(25)27-3/h4-5,8,11-12,15,17,20,23H,6-7,9-10H2,1-3H3/t12-,15-,17-,20-/m0/s1 |
| InChIKey | DTDADHMBRZKXSC-GKASHWOUSA-N |
| Formula | C22H26N2O4 |
| HBA | 5 |
| HBD | 1 |
| MW | 382.46 |
| Rotatable Bonds | 2 |
| TPSA | 63.79 |
| LogP | 3.19 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 382.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Rauvolfia caffra | Apocynaceae | Plantae | 947877 |
Showing of synonyms
10-methoxytetrahydroalstonine
Aricine
482-91-7
Heterophylline
Aricin
Quinovatine
ARICINE [MI]
NSC-72136
BUW4ULQ00A
Methyl (1S,15S,16S,20S)-7-methoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4(9),5,7,18-pentaene-19-carboxylate
4-methoxy-6-(3-pyridyl)pyran-2-one
(19.ALPHA.,20.ALPHA.)-16,17-DIDEHYDRO-10-METHOXY-19-METHYLOXAYOHIMBAN-16-CARBOXYLIC ACID METHYL ESTER
Methyl (1S,15S,16S,20S)-7-methoxy-16-methyl-17-oxa-3,13-diazapentacyclo(11.8.0.02,10.04,9.015,20)henicosa-2(10),4(9),5,7,18-pentaene-19-carboxylate
1,6-dihydroxy-7-methoxy-2-methylanthraquinone
16,17-didehydro-10-methoxy-19 alpha-methyloxayohimban-16-carboxylic acid
(19ALPHA,20ALPHA)-16,17-DIDEHYDRO-10-METHOXY-19-METHYLOXAYOHIMBAN-16-CARBOXYLIC ACID METHYL ESTER
(1R)-4b,8Abeta,9,9-tetramethyl-4aalpha,6a-(epoxymethano)decahydronaphthalene-1b,2b,5a,8a-tetrol 1-acetate 2,5-dinicotinate 8-benzoate
(1R)-4b,8Abeta,9,9-tetramethyl-4aalpha,6a-(epoxymethano)decahydronaphthalene-1b,2b,5a,8a-tetrol 1-acetic acid 2,5-dinicotinic acid 8-benzoic acid
(1R)-4beta,8Abeta,9,9-tetramethyl-4aalpha,6alpha-(epoxymethano)decahydronaphthalene-1beta,2beta,5alpha,8alpha-tetrol 1-acetic acid 2,5-dinicotinic acid 8-benzoic acid
Oxayohimban-16-carboxylic acid, 16,17-didehydro-10-methoxy-19-methyl-, methyl ester, (19alpha,20alpha)-(9CI)
16,17-didehydro-10-methoxy-19alpha-methyloxayohimban-16-carboxylic acid
Aricine (8ci)
Cinchovatin
Cinchovatine
Heterophylline (van)
Nsc 15624
Nsc 72136
Oxayohimban-16-carboxylic acid, 16,17-didehydro-10-methoxy-19-methyl-, methyl ester, (19alpha,20alpha)-
Unii-buw4ulq00a
Heterophylline (Rauwolfia)
NSC72136
CHEBI:2821
AC1L5K58
CHEMBL525626
SCHEMBL17089219
HY-N8720
BDBM50480269
AKOS032948537
FS-9922
DA-48550
CS-0148970
C09037
Q27105835
Oxayohimban-16-carboxylic acid, 16, 17-didehydro-10-methoxy-19-methyl-, methyl ester, (19.alpha., 20.alpha.)-
Oxayohimban-16-carboxylic acid,17-didehydro-10-methoxy-19-methyl-, methyl ester, (19.alpha.,20.alpha.)-
Pubchem:
251575
Cas:
482-91-7
Zinc:
ZINC000053201251
Kegg Ligand:
C09037
Chebi:
2821
Nmrshiftdb2:
60063046
Metabolights:
MTBLC2821
Chembl:
CHEMBL525626
Bindingdb:
50480269
No compound-protein relationship available.
SMILES: c1cccc2[nH]c(c3c12)C4N(CC3)CC5C(C4)C=COC5
Level: 0
Mol. Weight: 382.46 g/mol
Antimicrobial
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.84
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.980
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.91
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.720
- Plasma Protein Binding
- 43.66
- 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
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.240
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.430
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.480
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.850
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- -25.680
- Rat (Acute)
- 2.770
- Rat (Chronic Oral)
- 1.880
- Fathead Minnow
- 4.060
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 437.560
- Hydration Free Energy
- -5.230
- Log(D) at pH=7.4
- 3.650
- Log(P)
- 3.21
- Log S
- -3.4
- Log(Vapor Pressure)
- -8.32
- Melting Point
- 201.96
- pKa Acid
- 10.25
- pKa Basic
- 7.61
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.9496 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.9474 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8788 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.8787 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.8730 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8678 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 3 | 0.8659 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8266 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8182 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8040 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7946 |
| AGAP003309-PA | A0A1U7F4W2 | A0A1U7F4W2_ANOGA | Anopheles gambiae | 3 | 0.7899 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7876 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7849 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 3 | 0.7684 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7623 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7609 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7596 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7568 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7555 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.7554 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7521 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7513 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.7453 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7417 |
| Cellular retinol-binding protein type II | Q8UVG6 | Q8UVG6_DANRE | Danio rerio | 3 | 0.7394 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.7342 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7297 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7294 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7282 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7280 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7275 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7245 |
| NAD(P) transhydrogenase subunit alpha part 1 | Q2RSB2 | PNTAA_RHORT | Rhodospirillum rubrum | 3 | 0.7210 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7185 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7099 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 3 | 0.7078 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7075 |