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Vindoline
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | COC(=O)[C@@]1(O)[C@H](OC(=O)C)[C@]2(CC)C=CCN3[C@@H]2[C@@]2([C@H]1N(C)c1c2ccc(c1)OC)CC3 |
|---|---|
| InChI | InChI=1S/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3/t19-,20+,21+,23+,24+,25-/m0/s1 |
| InChIKey | CXBGOBGJHGGWIE-ACSXSLCXSA-N |
| Formula | C25H32N2O6 |
| HBA | 8 |
| HBD | 1 |
| MW | 456.54 |
| Rotatable Bonds | 4 |
| TPSA | 88.54 |
| LogP | 1.64 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.6 |
| Exact Mass | 456.23 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Catharanthus roseus | Apocynaceae | Plantae | 4058 |
Showing of synonyms
Vindoline
Vindolin
2182-14-1
(-)-Vindoline
571PJ1LW03
NSC91994
VINDOLINE [MI]
NSC 91994
NSC-91994
UNII-571PJ1LW03
CHEBI:16380
EINECS 218-558-0
NSC 628056
NSC-628056
(2.BETA.,3.BETA.,4.BETA.,5.ALPHA.,12.BETA.,19.ALPHA.)-4-(ACETYLOXY)-6,7-DIDEHYDRO-3-HYDROXY-16-METHOXY-1-METHYLASPIDOSPERMIDINE-3-CARBOXYLIC ACID METHYL ESTER
(2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylic acid
ASPIDOSPERMIDINE-3-CARBOXYLIC ACID, 4-(ACETYLOXY)-6,7-DIDEHYDRO-3-HYDROXY-16-METHOXY-1-METHYL-, METHYL ESTER, (2.BETA.,3.BETA.,4.BETA.,5.ALPHA.,12R,19.ALPHA.)-
Methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
Methyl 4beta-acetyloxy-3beta-hydroxy-16-methoxy-1-methyl-6,7-didehydro-2beta,5alpha,12beta,19alpha-aspidospermidine-3alpha-carboxylate
NSC628056
Methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo(10.6.1.01,9.02,7.016,19)nonadeca-2(7),3,5,13-tetraene-10-carboxylate
Methyl (3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-5-hydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino(8,1-cd)carbazole-5-carboxylate
Methyl (3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-5-hydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
Methyl 11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo(10.6.1.0,.0,.0,)nonadeca-2(7),3,5,13-tetraene-10-carboxylic acid
Methyl 11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0,.0,.0,]nonadeca-2(7),3,5,13-tetraene-10-carboxylic acid
Vindoline (8CI)
Vindoline, citrate, (2beta,3beta,4beta,5alpha,12beta,19alpha)-isomer
Vindoline, monohydrochloride, (2beta,3beta,4beta,5alpha,12beta,19alpha)-isomer
(2 beta,3 beta,4 beta,5 alpha,12 beta,19 alpha)-4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylic acid
(2BETA,3BETA,4BETA,5ALPHA,12BETA,19ALPHA)-4-(ACETYLOXY)-6,7-DIDEHYDRO-3-HYDROXY-16-METHOXY-1-METHYLASPIDOSPERMIDINE-3-CARBOXYLIC ACID METHYL ESTER
10197-89-4
218-558-0
ASPIDOSPERMIDINE-3-CARBOXYLIC ACID, 4-(ACETYLOXY)-6,7-DIDEHYDRO-3-HYDROXY-16-METHOXY-1-METHYL-, METHYL ESTER, (2BETA,3BETA,4BETA,5ALPHA,12R,19ALPHA)-
SR-05000002168
SCHEMBL234532
MEGxp0_001802
CHEMBL2001832
ACon1_000494
DTXSID901045589
57794-53-3
Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)-
HY-N0687
Methyl 4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
Vindoline, >=98.0% (HPLC)
MFCD27991347
NSC823866
S3970
AKOS032962057
CCG-208615
FV10830
NSC-823866
SMP2_000150
NCGC00163666-02
NCI60_042033
CS-0009711
SR-05000002168-2
SR-05000002168-3
BRD-K64280411-001-01-7
Q15427936
(2?,3?,4?,5?,12?,19?)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1 -methyl-aspidospermidine-3-carboxylic acid methyl ester
Aspidospermidine-3-carboxylic acid,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2.beta.,3.beta.,4.beta.,5.alpha.,12.beta.,19.alpha.)-
Methyl (3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-5-hydroxy-8- methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1- cd]carbazole-5-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:
260535
Cas:
2182-14-1
Gnps:
CCMSLIB00006520716
Zinc:
ZINC000053201238
Kegg Ligand:
C01626
Chebi:
16380
Nmrshiftdb2:
60027819
Metabolights:
MTBLC16380
Chembl:
CHEMBL2001832
CPRiL:
102949
SMILES: c1cccc(c1C234)NC3CCC5C2N(CC4)CC=C5
Level: 0
Mol. Weight: 456.54 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.87
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.840
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.84
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.740
- Plasma Protein Binding
- 54.56
- 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
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.800
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.010
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.090
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.180
- 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
- Toxic
- T. Pyriformis
- -188.040
- Rat (Acute)
- 3.320
- Rat (Chronic Oral)
- 1.830
- Fathead Minnow
- 3.970
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 452.410
- Hydration Free Energy
- -2.810
- Log(D) at pH=7.4
- 2.340
- Log(P)
- 1.72
- Log S
- -2.68
- Log(Vapor Pressure)
- -9.11
- Melting Point
- 184.46
- pKa Acid
- 5.95
- pKa Basic
- 6.41
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8645 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 4 | 0.8536 |
| Acidic mammalian chitinase | Q9BZP6 | CHIA_HUMAN | Homo sapiens | 3 | 0.8389 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7678 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7631 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7604 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7568 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7533 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7342 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7330 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7298 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7281 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7240 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7217 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7192 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7192 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7188 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7187 |
| ADP compounds hydrolase NudE | P45799 | NUDE_ECOLI | Escherichia coli | 2 | 0.7178 |
| Caffeoyl-CoA O-methyltransferase | Q40313 | CAMT_MEDSA | Medicago sativa | 3 | 0.7137 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7126 |
| Cytochrome P450 monooxygenase PikC | O87605 | PIKC_STRVZ | Streptomyces venezuelae | 3 | 0.7113 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7076 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7067 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7064 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7061 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7059 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7039 |
| Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 3 | 0.7018 |