Gelsebamine

Details

• Internal ID: a2923b31-89f5-42c8-bd1e-18b7ab7bf59f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3R,3aS,4R,5S,6aS)-3-(diethylaminomethyl)-4-(hydroxymethyl)-5-methyl-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• InChI: InChI=1S/C14H25NO3/c1-4-15(5-2)7-10-13-11(8-16)9(3)6-12(13)18-14(10)17/h9-13,16H,4-8H2,1-3H3/t9-,10-,11+,12-,13+/m0/s1
• InChI Key: GDLVNWBONOJNFR-IEECTRCBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₅NO₃
• Molecular Weight: 255.35 g/mol
• Exact Mass: 255.18344366 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.13
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• (3R,3aS,4R,5S,6aS)-3-(diethylaminomethyl)-4-(hydroxymethyl)-5-methyl-3,3a,4,5,6,6a-hexahydrocyclopenta(b)furan-2-one
• (3R,3aS,4R,5S,6aS)-3-(diethylaminomethyl)-4-(hydroxymethyl)-5-methyl-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• RefChem:142839
• CHEMBL503405

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9438	94.38%
Caco-2	+	0.7468	74.68%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Lysosomes	0.6278	62.78%
OATP2B1 inhibitior	-	0.8500	85.00%
OATP1B1 inhibitior	+	0.9120	91.20%
OATP1B3 inhibitior	+	0.9471	94.71%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8888	88.88%
P-glycoprotein inhibitior	-	0.9402	94.02%
P-glycoprotein substrate	-	0.8151	81.51%
CYP3A4 substrate	-	0.5349	53.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6613	66.13%
CYP3A4 inhibition	-	0.8436	84.36%
CYP2C9 inhibition	-	0.8406	84.06%
CYP2C19 inhibition	-	0.8334	83.34%
CYP2D6 inhibition	-	0.8598	85.98%
CYP1A2 inhibition	-	0.6444	64.44%
CYP2C8 inhibition	-	0.9421	94.21%
CYP inhibitory promiscuity	-	0.9243	92.43%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5907	59.07%
Eye corrosion	-	0.9651	96.51%
Eye irritation	-	0.6149	61.49%
Skin irritation	-	0.7491	74.91%
Skin corrosion	-	0.8829	88.29%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5570	55.70%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8214	82.14%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.6175	61.75%
Acute Oral Toxicity (c)	III	0.6055	60.55%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.6181	61.81%
Thyroid receptor binding	-	0.6110	61.10%
Glucocorticoid receptor binding	-	0.6851	68.51%
Aromatase binding	-	0.8908	89.08%
PPAR gamma	-	0.8991	89.91%
Honey bee toxicity	-	0.9243	92.43%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.6465	64.65%

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	94.12%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.53%	97.25%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.76%	89.34%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.18%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.02%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.43%	91.11%
CHEMBL2581	P07339	Cathepsin D	84.13%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.61%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.77%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.72%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.98%	100.00%

Plants that contains it

• Gelsemium elegans

Cross-Links

• PubChem: 16086588
• NPASS: NPC203170
• ChEMBL: CHEMBL503405