(1S,3R,5S,8R,9R,11S,12S)-3-hydroxy-1',5-dimethylspiro[6-oxa-2-azatetracyclo[6.5.0.02,11.04,9]tridecane-12,3'-indole]-2'-one

Details

• Internal ID: 74435b1a-f789-46e9-a3ad-aa30e2c74193
• Taxonomy: Alkaloids and derivatives > Gelsemium alkaloids
• IUPAC Name: (1S,3R,5S,8R,9R,11S,12S)-3-hydroxy-1',5-dimethylspiro[6-oxa-2-azatetracyclo[6.5.0.02,11.04,9]tridecane-12,3'-indole]-2'-one
• SMILES (Canonical): CC1C2C3CC4C5(CC(C3CO1)N4C2O)C6=CC=CC=C6N(C5=O)C
• SMILES (Isomeric): C[C@H]1C2[C@@H]3C[C@H]4[C@]5(C[C@@H]([C@@H]3CO1)N4[C@@H]2O)C6=CC=CC=C6N(C5=O)C
• InChI: InChI=1S/C20H24N2O3/c1-10-17-11-7-16-20(8-15(12(11)9-25-10)22(16)18(17)23)13-5-3-4-6-14(13)21(2)19(20)24/h3-6,10-12,15-18,23H,7-9H2,1-2H3/t10-,11+,12+,15-,16-,17?,18+,20-/m0/s1
• InChI Key: KMTRWCJWJKYMFP-UIAFLIATSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄N₂O₃
• Molecular Weight: 340.40 g/mol
• Exact Mass: 340.17869263 g/mol
• Topological Polar Surface Area (TPSA): 53.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.35
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9588	95.88%
Caco-2	+	0.7989	79.89%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5819	58.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8811	88.11%
OATP1B3 inhibitior	+	0.9468	94.68%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.6055	60.55%
P-glycoprotein inhibitior	-	0.7947	79.47%
P-glycoprotein substrate	+	0.5429	54.29%
CYP3A4 substrate	+	0.6421	64.21%
CYP2C9 substrate	-	0.8129	81.29%
CYP2D6 substrate	-	0.7871	78.71%
CYP3A4 inhibition	-	0.8788	87.88%
CYP2C9 inhibition	-	0.8277	82.77%
CYP2C19 inhibition	-	0.7527	75.27%
CYP2D6 inhibition	-	0.8329	83.29%
CYP1A2 inhibition	-	0.8132	81.32%
CYP2C8 inhibition	-	0.7980	79.80%
CYP inhibitory promiscuity	-	0.8772	87.72%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6616	66.16%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9930	99.30%
Skin irritation	-	0.8142	81.42%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	+	0.6463	64.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.4357	43.57%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	-	0.5194	51.94%
skin sensitisation	-	0.8620	86.20%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8066	80.66%
Acute Oral Toxicity (c)	III	0.5124	51.24%
Estrogen receptor binding	+	0.7670	76.70%
Androgen receptor binding	+	0.6600	66.00%
Thyroid receptor binding	+	0.5904	59.04%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.4847	48.47%
Honey bee toxicity	-	0.8455	84.55%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9028	90.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.35%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.85%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.11%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.29%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.61%	86.33%
CHEMBL4208	P20618	Proteasome component C5	83.37%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.70%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.68%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.63%	82.69%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.15%	100.00%

Plants that contains it

• Alstonia angustifolia

Cross-Links

• PubChem: 118715151
• LOTUS: LTS0033362
• wikiData: Q105143200