Select a section from the left sidebar
Spegatrine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Monoterpenoid Indole Alkaloid
| Canonical Smiles | OC[C@@H]1[C@@H]2C[C@@H]3[N+](C1Cc1c3[nH]c3c1cc(O)cc3)(C/C/2=C/C)C |
|---|---|
| InChI | InChI=1S/C20H24N2O2/c1-3-11-9-22(2)18-8-15-14-6-12(24)4-5-17(14)21-20(15)19(22)7-13(11)16(18)10-23/h3-6,13,16,18-19,21,23H,7-10H2,1-2H3/p+1/b11-3-/t13-,16-,18?,19+,22?/m1/s1 |
| InChIKey | DOTYYDUNWITJSJ-SYMHJQAPSA-O |
| Formula | C20H25N2O2+ |
| HBA | 2 |
| HBD | 3 |
| MW | 325.43 |
| Rotatable Bonds | 1 |
| TPSA | 56.25 |
| LogP | 2.87 |
| Number Rings | 6 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 24 |
| Formal Charge | 1 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 325.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Pleiocarpa pycnantha | Apocynaceae | Plantae | 1220085 |
| 2 | Tabernaemontana contorta | Apocynaceae | Plantae | 761060 |
Showing of synonyms
Spegatrine
47326-53-4
(1S,13R,14S,15E)-15-ethylidene-13-(hydroxymethyl)-17-methyl-3-aza-17-azoniapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4(9),5,7-tetraen-7-ol
Sarpaganium, 10,17-dihydroxy-4-methyl-
(1S,13R,14S,15E)-15-ethylidene-13-(hydroxymethyl)-17-methyl-3-aza-17-azoniapentacyclo(12.3.1.02,10.04,9.012,17)octadeca-2(10),4(9),5,7-tetraen-7-ol
SCHEMBL25365744
AKOS032948989
Q15427854
- Ndongo JT, Mbing JN, et al. (2018). Carbazole-, aspidofractinine-, and aspidocarpamine-type alkaloids from Pleiocarpa pycnantha.. Journal of natural products,2018, 81(5), 1193-1202. [View] [PubMed]
- Foudjo Melacheu G, Mfotie Njoya E, et al. (2021). Contortamide, a new anti-colon cancer cerebroside and other constituents from Tabernaemontana contorta Stapf (Apocynaceae). Natural product research,2021, 35(11), 1757-1765. [View] [PubMed]
No compound-protein relationship available.
SMILES: C=C(C1)C(C2)CC(C3)[NH+]1C2c(c3c45)[nH]c4cccc5
Level: 0
Mol. Weight: 325.43 g/mol
Anti-colon cancer
Absorption
- Caco-2 (logPapp)
- -5.74
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.170
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.09
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.190
- Plasma Protein Binding
- 49.5
- 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
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 15.580
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- 0.860
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.350
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.550
- 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
- 0.280
- Rat (Acute)
- 2.860
- Rat (Chronic Oral)
- 2.200
- Fathead Minnow
- 4.400
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 449.900
- Hydration Free Energy
- -7.180
- Log(D) at pH=7.4
- 0.740
- Log(P)
- -0.73
- Log S
- -1.59
- Log(Vapor Pressure)
- -11.54
- Melting Point
- 339.65
- pKa Acid
- 7.96
- pKa Basic
- 7.0
| 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 | 0.9421 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.9052 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.8992 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.8687 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8179 |
| Naphthalene 1,2-dioxygenase system, large oxygenase component | P0A110 | NDOB_PSEPU | Pseudomonas putida | 3 | 0.7988 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7793 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7479 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7475 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7434 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7373 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7334 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7324 |
| Glutamate receptor 2 | P42262 | GRIA2_HUMAN | Homo sapiens | 3 | 0.7324 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 2 | 0.7241 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7224 |
| Rho-associated protein kinase 1 | Q13464 | ROCK1_HUMAN | Homo sapiens | 3 | 0.7053 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 2 | 0.7016 |