Vindolinine. 19-epimer, N-oxide

Details

• Internal ID: 65064d93-a185-43a5-8046-6b471ec97eba
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Carbazoles
• IUPAC Name: methyl (1R,9R,10S,12R,19S,20R)-20-methyl-16-oxido-8-aza-16-azoniahexacyclo[10.6.1.19,12.01,9.02,7.016,19]icosa-2,4,6,13-tetraene-10-carboxylate
• SMILES (Canonical): CC1C23CC(C14C5(C2[N+](CC5)(CC=C3)[O-])C6=CC=CC=C6N4)C(=O)OC
• SMILES (Isomeric): C[C@@H]1[C@]23C[C@@H]([C@@]14[C@@]5([C@H]2[N+](CC5)(CC=C3)[O-])C6=CC=CC=C6N4)C(=O)OC
• InChI: InChI=1S/C21H24N2O3/c1-13-19-8-5-10-23(25)11-9-20(18(19)23)14-6-3-4-7-16(14)22-21(13,20)15(12-19)17(24)26-2/h3-8,13,15,18,22H,9-12H2,1-2H3/t13-,15-,18+,19+,20-,21-,23?/m1/s1
• InChI Key: JOAAIYRFWUHKSF-IVTYPWQJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄N₂O₃
• Molecular Weight: 352.40 g/mol
• Exact Mass: 352.17869263 g/mol
• Topological Polar Surface Area (TPSA): 56.40 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.57
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 16-epi-19-S-Vindolinine-N-oxide
• 88720-99-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6078	60.78%
Caco-2	+	0.5721	57.21%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.4434	44.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8862	88.62%
OATP1B3 inhibitior	+	0.9339	93.39%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6493	64.93%
P-glycoprotein inhibitior	-	0.8268	82.68%
P-glycoprotein substrate	+	0.5888	58.88%
CYP3A4 substrate	+	0.6633	66.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8225	82.25%
CYP3A4 inhibition	-	0.8714	87.14%
CYP2C9 inhibition	-	0.8392	83.92%
CYP2C19 inhibition	-	0.8312	83.12%
CYP2D6 inhibition	-	0.6898	68.98%
CYP1A2 inhibition	-	0.7764	77.64%
CYP2C8 inhibition	+	0.6467	64.67%
CYP inhibitory promiscuity	-	0.9234	92.34%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5838	58.38%
Eye corrosion	-	0.9824	98.24%
Eye irritation	-	0.9952	99.52%
Skin irritation	-	0.7668	76.68%
Skin corrosion	-	0.9284	92.84%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3600	36.00%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8357	83.57%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.6959	69.59%
Acute Oral Toxicity (c)	III	0.5779	57.79%
Estrogen receptor binding	-	0.5729	57.29%
Androgen receptor binding	+	0.7364	73.64%
Thyroid receptor binding	+	0.5519	55.19%
Glucocorticoid receptor binding	+	0.6921	69.21%
Aromatase binding	+	0.5741	57.41%
PPAR gamma	-	0.5904	59.04%
Honey bee toxicity	-	0.8672	86.72%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5904	59.04%
Fish aquatic toxicity	+	0.9655	96.55%

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	97.90%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.26%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	95.70%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.34%	95.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.98%	93.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.44%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.32%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.54%	99.23%
CHEMBL4208	P20618	Proteasome component C5	81.02%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.90%	94.45%
CHEMBL230	P35354	Cyclooxygenase-2	80.74%	89.63%

Plants that contains it

• Catharanthus roseus

Cross-Links

• PubChem: 78358538
• NPASS: NPC199616