(1R,2S,4S,6R,7R,8S)-6-[(1R)-1-hydroxyethyl]-6-(hydroxymethyl)-1',6'-dimethoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undecane-2,3'-indole]-2'-one

Details

• Internal ID: acf58706-99e7-4d9e-a1e8-c91db8b9af4e
• Taxonomy: Alkaloids and derivatives > Gelsemium alkaloids
• IUPAC Name: (1R,2S,4S,6R,7R,8S)-6-[(1R)-1-hydroxyethyl]-6-(hydroxymethyl)-1',6'-dimethoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undecane-2,3'-indole]-2'-one
• SMILES (Canonical): CC(C1(C2CC3C4(CC(C2CO3)N1)C5=C(C=C(C=C5)OC)N(C4=O)OC)CO)O
• SMILES (Isomeric): C[C@H]([C@@]1([C@@H]2C[C@@H]3[C@]4(C[C@@H]([C@H]2CO3)N1)C5=C(C=C(C=C5)OC)N(C4=O)OC)CO)O
• InChI: InChI=1S/C21H28N2O6/c1-11(25)21(10-24)15-7-18-20(8-16(22-21)13(15)9-29-18)14-5-4-12(27-2)6-17(14)23(28-3)19(20)26/h4-6,11,13,15-16,18,22,24-25H,7-10H2,1-3H3/t11-,13+,15-,16+,18-,20+,21-/m1/s1
• InChI Key: GWYGPYIOBSALOZ-DMLIBQJSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈N₂O₆
• Molecular Weight: 404.50 g/mol
• Exact Mass: 404.19473662 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.35
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7876	78.76%
Caco-2	-	0.5304	53.04%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.4030	40.30%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8843	88.43%
OATP1B3 inhibitior	+	0.9406	94.06%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6489	64.89%
P-glycoprotein inhibitior	-	0.6702	67.02%
P-glycoprotein substrate	+	0.6412	64.12%
CYP3A4 substrate	+	0.6829	68.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3897	38.97%
CYP3A4 inhibition	-	0.7244	72.44%
CYP2C9 inhibition	-	0.7505	75.05%
CYP2C19 inhibition	-	0.7485	74.85%
CYP2D6 inhibition	-	0.8240	82.40%
CYP1A2 inhibition	-	0.8435	84.35%
CYP2C8 inhibition	-	0.6288	62.88%
CYP inhibitory promiscuity	-	0.8222	82.22%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5780	57.80%
Eye corrosion	-	0.9826	98.26%
Eye irritation	-	0.9720	97.20%
Skin irritation	-	0.7708	77.08%
Skin corrosion	-	0.9278	92.78%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6711	67.11%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.6449	64.49%
skin sensitisation	-	0.8401	84.01%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.9337	93.37%
Acute Oral Toxicity (c)	III	0.5967	59.67%
Estrogen receptor binding	+	0.8663	86.63%
Androgen receptor binding	+	0.7050	70.50%
Thyroid receptor binding	+	0.5348	53.48%
Glucocorticoid receptor binding	+	0.6446	64.46%
Aromatase binding	+	0.6242	62.42%
PPAR gamma	+	0.7360	73.60%
Honey bee toxicity	-	0.7717	77.17%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.7589	75.89%

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	99.33%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.91%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.54%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.33%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.22%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.56%	94.45%
CHEMBL4208	P20618	Proteasome component C5	93.19%	90.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.50%	97.25%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	92.42%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.21%	95.56%
CHEMBL4581	P52732	Kinesin-like protein 1	89.53%	93.18%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.41%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.17%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.95%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.44%	92.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.25%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.06%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.97%	97.14%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.63%	96.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.50%	99.15%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.22%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.62%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	81.32%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.23%	99.17%
CHEMBL226	P30542	Adenosine A1 receptor	80.99%	95.93%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.95%	91.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.60%	91.07%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.55%	95.71%
CHEMBL2535	P11166	Glucose transporter	80.07%	98.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.02%	93.99%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.01%	90.24%

Plants that contains it

• Gelsemium elegans
• Glycyrrhiza yunnanensis

Cross-Links

• PubChem: 11090753
• NPASS: NPC184398
• LOTUS: LTS0188270
• wikiData: Q105022908