Stemonidine

Details

• Internal ID: 794ca3b8-9fba-43c6-9cd7-4ba63105d4d9
• Taxonomy: Alkaloids and derivatives > Stemona alkaloids > Tuberostemospironine-type alkaloids > Croomine-type alkaloids
• IUPAC Name: (3S,3'S,8S,9R,9aR)-8-methoxy-3'-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]spiro[1,2,3,5,6,7,8,9a-octahydropyrrolo[1,2-a]azepine-9,5'-oxolane]-2'-one
• SMILES (Canonical): CC1CC(OC1=O)C2CCC3N2CCCC(C34CC(C(=O)O4)C)OC
• SMILES (Isomeric): C[C@H]1C[C@H](OC1=O)[C@@H]2CC[C@H]3N2CCC[C@@H]([C@@]34C[C@@H](C(=O)O4)C)OC
• InChI: InChI=1S/C19H29NO5/c1-11-9-14(24-17(11)21)13-6-7-15-19(10-12(2)18(22)25-19)16(23-3)5-4-8-20(13)15/h11-16H,4-10H2,1-3H3/t11-,12-,13-,14-,15+,16-,19+/m0/s1
• InChI Key: TZPKEJFBTXRNTK-OSPICLMDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₉NO₅
• Molecular Weight: 351.40 g/mol
• Exact Mass: 351.20457303 g/mol
• Topological Polar Surface Area (TPSA): 65.10 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.90
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 66267-46-7
• (3S,3'S,8S,9R,9aR)-8-methoxy-3'-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]spiro[1,2,3,5,6,7,8,9a-octahydropyrrolo[1,2-a]azepine-9,5'-oxolane]-2'-one
• Q-100758

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8199	81.99%
Caco-2	+	0.6039	60.39%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4569	45.69%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.9038	90.38%
OATP1B3 inhibitior	+	0.9343	93.43%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.6106	61.06%
P-glycoprotein inhibitior	-	0.7197	71.97%
P-glycoprotein substrate	-	0.6424	64.24%
CYP3A4 substrate	+	0.6417	64.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6632	66.32%
CYP3A4 inhibition	-	0.7081	70.81%
CYP2C9 inhibition	-	0.8865	88.65%
CYP2C19 inhibition	-	0.8682	86.82%
CYP2D6 inhibition	-	0.9414	94.14%
CYP1A2 inhibition	-	0.7375	73.75%
CYP2C8 inhibition	-	0.8246	82.46%
CYP inhibitory promiscuity	-	0.9628	96.28%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5476	54.76%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.9601	96.01%
Skin irritation	-	0.7790	77.90%
Skin corrosion	-	0.9172	91.72%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.8250	82.50%
skin sensitisation	-	0.8608	86.08%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.7094	70.94%
Acute Oral Toxicity (c)	III	0.6332	63.32%
Estrogen receptor binding	+	0.6477	64.77%
Androgen receptor binding	+	0.6984	69.84%
Thyroid receptor binding	+	0.5466	54.66%
Glucocorticoid receptor binding	+	0.7288	72.88%
Aromatase binding	-	0.5431	54.31%
PPAR gamma	-	0.6432	64.32%
Honey bee toxicity	-	0.8115	81.15%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.7200	72.00%
Fish aquatic toxicity	+	0.6722	67.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.31%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.13%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.81%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.67%	95.56%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	90.89%	86.00%
CHEMBL1871	P10275	Androgen Receptor	90.80%	96.43%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.31%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.72%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	89.01%	93.04%
CHEMBL204	P00734	Thrombin	88.73%	96.01%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.78%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	84.44%	92.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.25%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.78%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.35%	94.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.25%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.93%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.76%	86.33%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.75%	82.38%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.42%	99.18%

Plants that contains it

• Stemona japonica
• Stemona tuberosa

Cross-Links

• PubChem: 24721470
• NPASS: NPC188658