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Catharanthine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | CCC1=C[C@@H]2CN3[C@H]1[C@@](C2)(C(=O)OC)c1[nH]c2c(c1CC3)cccc2 |
|---|---|
| InChI | InChI=1S/C21H24N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13-,19+,21-/m0/s1 |
| InChIKey | CMKFQVZJOWHHDV-NQZBTDCJSA-N |
| Formula | C21H24N2O2 |
| HBA | 3 |
| HBD | 1 |
| MW | 336.44 |
| Rotatable Bonds | 2 |
| TPSA | 45.33 |
| LogP | 3.18 |
| Number Rings | 6 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.48 |
| Exact Mass | 336.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Catharanthus roseus | Apocynaceae | Plantae | 4058 |
Showing of synonyms
Catharanthine
2468-21-5
(+)-3,4-Didehydrocoronaridine
(+)-Catharanthine
WT0YJV846J
Catharanthine, (+)-
EINECS 219-586-6
CATHARANTHINE [MI]
CHEBI:3469
DTXSID80947621
Methyl (2-alpha,5-beta,6-alpha,18-beta)-3,4-didehydroibogamine-18-carboxylate
Methyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate
Ibogamine-18-carboxylic acid, 3,4-didehydro-, methyl ester, (2-alpha,5-beta,6-alpha,18-beta)-
IBOGAMINE-18-CARBOXYLIC ACID, 3,4-DIDEHYDRO-, METHYL ESTER,(2.ALPHA.,5.BETA.,6.ALPHA.,18.BETA.)-
Methyl (2alpha,18beta)-3,4-didehydroibogamine-18-carboxylate
Methyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate
DTXCID401527514
IBOGAMINE-18-CARBOXYLIC ACID, 3,4-DIDEHYDRO-, METHYL ESTER,(2ALPHA,5BETA,6ALPHA,18BETA)-
Catharanthin
Catharanthine Base
Ibogamine-18-carboxylic acid, 3,4-didehydro-, methyl ester, (2alpha,5beta,6alpha,18beta)-
CHEMBL2163793
UNII-WT0YJV846J
MFCD01753356
Catharanthine (free base)
Catharanthine, >=95% (HPLC)
HMS2095F15
HMS3652A13
HMS3712F15
HMS3885K13
BDBM50396009
MSK168797
NSC823867
S3202
AKOS024463388
Methyl (2alpha,5beta,6alpha)-3,4-didehydroibogamine-18beta-carboxylate
CCG-220187
FC10810
NSC-823867
AC-34053
1ST168797
NS00018340
SW198653-2
AB01566866_01
BRD-K92377961-001-02-9
BRD-K92377961-001-03-7
Ibogamine-18-carboxylic acid, 3,4-didehydro-, methyl ester, (2|A,5|A,6|A,18|A)-
Methyl (2?,5?,6?)-3,4-didehydroibogamine-18?-carboxylate
(6R,6aR,9R,11R)-Methyl 7-ethyl-6,6a,9,10,12,13-hexahydro-5H-6,9-methanopyrido[1',2':1,2]azepino[4,5-b]indole-6-carboxylate
(6R,6aR,9R,11R)-Methyl7-ethyl-6,6a,9,10,12,13-hexahydro-5H-6,9-methanopyrido[1',2':1,2]azepino[4,5-b]indole-6-carboxylate
- Hanafy M, Matter M, et al. (2016). Production of indole alkaloids in hairy root cultures of Catharanthus roseus L. and their antimicrobial activity. South African Journal of Botany, 2016, 105, 9-18. [View]
Pubchem:
5458190
Cas:
2468-21-5
Gnps:
CCMSLIB00000853326
Zinc:
ZINC000057297068
Chebi:
3469
Metabolights:
MTBLC3469
Chembl:
CHEMBL2163793
Bindingdb:
50396009
Selleck:
catharanthine
CPRiL:
85319
SMILES: c1cccc2[nH]c(c3c12)C4C5N(CC3)CC(C4)C=C5
Level: 0
Mol. Weight: 336.44 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.87
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.95
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.97
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.94
- Plasma Protein Binding
- 57.87
- 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
- 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
- 9.77
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.72
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.98
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.22
- 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
- -3.78
- Rat (Acute)
- 2.81
- Rat (Chronic Oral)
- 1.92
- Fathead Minnow
- 4.1
- 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
- 421.13
- Hydration Free Energy
- -5.85
- Log(D) at pH=7.4
- 3.36
- Log(P)
- 3.34
- Log S
- -3.66
- Log(Vapor Pressure)
- -8.3
- Melting Point
- 197.16
- pKa Acid
- 10.17
- pKa Basic
- 6.46
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8476 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7878 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 3 | 0.7684 |
| Retinol-binding protein 1 | P09455 | RET1_HUMAN | Homo sapiens | 3 | 0.7664 |
| Aldo-keto reductase family 1 member B10 | O60218 | AK1BA_HUMAN | Homo sapiens | 3 | 0.7648 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7623 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7616 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7531 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7526 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7507 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7434 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7292 |
| Caspase-7 | P55210 | CASP7_HUMAN | Homo sapiens | 3 | 0.7168 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7119 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7097 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7057 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7031 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7003 |