Vindoline

Details

• Internal ID: 8b327ae0-6d96-4ada-9a5f-7f3d2957615b
• Taxonomy: Alkaloids and derivatives > Plumeran-type alkaloids
• IUPAC Name: 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
• SMILES (Canonical): CCC12C=CCN3C1C4(CC3)C(C(C2OC(=O)C)(C(=O)OC)O)N(C5=C4C=CC(=C5)OC)C
• SMILES (Isomeric): CC[C@@]12C=CCN3[C@@H]1[C@]4(CC3)[C@H]([C@]([C@@H]2OC(=O)C)(C(=O)OC)O)N(C5=C4C=CC(=C5)OC)C
• 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
• InChI Key: CXBGOBGJHGGWIE-ACSXSLCXSA-N
• Popularity: 175 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂N₂O₆
• Molecular Weight: 456.50 g/mol
• Exact Mass: 456.22603674 g/mol
• Topological Polar Surface Area (TPSA): 88.50 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.64
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 2182-14-1
• Vindolin
• (-)-Vindoline
• 571PJ1LW03
• NSC91994
• NSC-91994
• CHEBI:16380
• DTXSID901045589
• NSC-628056
• (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylic acid
• 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 (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
• RefChem:194275
• DTXCID101527515
• (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
• 218-558-0
• MFCD27991347
• SR-05000002168
• C25H32N2O6
• 57794-53-3
• NSC 91994
• VINDOLINE [MI]
• SCHEMBL234532
• UNII-571PJ1LW03
• MEGxp0_001802
• CHEMBL2001832
• ACon1_000494
• 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)
• EINECS 218-558-0
• NSC823866
• s3970
• AKOS032962057
• CCG-208615
• FV10830
• NSC 628056
• NSC-823866
• SMP2_000150
• NCGC00163666-02
• NCI60_042033
• SY074219
• CS-0009711
• SR-05000002168-2
• SR-05000002168-3
• BRD-K64280411-001-01-7
• Q15427936
• (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
• (2?,3?,4?,5?,12?,19?)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1 -methyl-aspidospermidine-3-carboxylic acid methyl ester;NSC91994;(-)-Vindoline
• 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.)-
• 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 (1R,9R,10S,11R,12R,19R)-11-acetoxy-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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6986	69.86%
Caco-2	+	0.5766	57.66%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7594	75.94%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.8943	89.43%
OATP1B3 inhibitior	+	0.9103	91.03%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.8341	83.41%
P-glycoprotein inhibitior	+	0.9511	95.11%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.6962	69.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6909	69.09%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.8781	87.81%
CYP2C19 inhibition	-	0.7769	77.69%
CYP2D6 inhibition	+	0.5829	58.29%
CYP1A2 inhibition	-	0.9135	91.35%
CYP2C8 inhibition	-	0.8437	84.37%
CYP inhibitory promiscuity	-	0.6839	68.39%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5312	53.12%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9626	96.26%
Skin irritation	-	0.8025	80.25%
Skin corrosion	-	0.9464	94.64%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7632	76.32%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.5801	58.01%
skin sensitisation	-	0.8714	87.14%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7719	77.19%
Acute Oral Toxicity (c)	III	0.7290	72.90%
Estrogen receptor binding	+	0.7804	78.04%
Androgen receptor binding	+	0.7492	74.92%
Thyroid receptor binding	+	0.5891	58.91%
Glucocorticoid receptor binding	+	0.7168	71.68%
Aromatase binding	+	0.5799	57.99%
PPAR gamma	+	0.6158	61.58%
Honey bee toxicity	-	0.8465	84.65%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9492	94.92%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.46%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.00%	91.11%
CHEMBL4208	P20618	Proteasome component C5	97.13%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.37%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.24%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.45%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.51%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.05%	94.00%
CHEMBL205	P00918	Carbonic anhydrase II	87.77%	98.44%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.36%	95.89%
CHEMBL2581	P07339	Cathepsin D	87.28%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.08%	97.09%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.92%	94.42%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.77%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.69%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.63%	95.89%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.63%	90.24%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.80%	93.65%
CHEMBL340	P08684	Cytochrome P450 3A4	80.02%	91.19%

Plants that contains it

• Catharanthus ovalis
• Catharanthus roseus

Cross-Links

• PubChem: 260535
• NPASS: NPC127996
• LOTUS: LTS0082987
• wikiData: Q15427936