Gelsemiol

Details

• Internal ID: f91760bf-75d9-442d-9f00-45f56bc6b92c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3R,3aS,4R,5S,6aS)-3,4-bis(hydroxymethyl)-5-methyl-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• SMILES (Canonical): CC1CC2C(C1CO)C(C(=O)O2)CO
• SMILES (Isomeric): C[C@H]1C[C@H]2[C@@H]([C@@H]1CO)[C@@H](C(=O)O2)CO
• InChI: InChI=1S/C10H16O4/c1-5-2-8-9(6(5)3-11)7(4-12)10(13)14-8/h5-9,11-12H,2-4H2,1H3/t5-,6+,7-,8-,9-/m0/s1
• InChI Key: FNYPTQQTJGQJNF-BGKGJTHRSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 200.23 g/mol
• Exact Mass: 200.10485899 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.22
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 110414-77-2
• (3R,3aS,4R,5S,6aS)-3,4-bis(hydroxymethyl)-5-methyl-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• (3R,3aS,4R,5S,6aS)-Hexahydro-3,4-bis(hydroxymethyl)-5-methyl-2H-cyclopenta[b]furan-2-one
• HY-N3938
• AKOS032962123
• FS-10138
• CS-0024485

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9485	94.85%
Caco-2	-	0.7445	74.45%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5594	55.94%
OATP2B1 inhibitior	-	0.8496	84.96%
OATP1B1 inhibitior	+	0.9372	93.72%
OATP1B3 inhibitior	+	0.9645	96.45%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.9067	90.67%
BSEP inhibitior	-	0.9517	95.17%
P-glycoprotein inhibitior	-	0.9720	97.20%
P-glycoprotein substrate	-	0.9270	92.70%
CYP3A4 substrate	-	0.5681	56.81%
CYP2C9 substrate	-	0.7874	78.74%
CYP2D6 substrate	-	0.8369	83.69%
CYP3A4 inhibition	-	0.9504	95.04%
CYP2C9 inhibition	-	0.9058	90.58%
CYP2C19 inhibition	-	0.8639	86.39%
CYP2D6 inhibition	-	0.9435	94.35%
CYP1A2 inhibition	-	0.8198	81.98%
CYP2C8 inhibition	-	0.9760	97.60%
CYP inhibitory promiscuity	-	0.9448	94.48%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6302	63.02%
Eye corrosion	-	0.9708	97.08%
Eye irritation	+	0.5917	59.17%
Skin irritation	-	0.7434	74.34%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.6228	62.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.7196	71.96%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.6742	67.42%
skin sensitisation	-	0.9116	91.16%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.6111	61.11%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.6466	64.66%
Acute Oral Toxicity (c)	III	0.4770	47.70%
Estrogen receptor binding	-	0.6415	64.15%
Androgen receptor binding	-	0.6242	62.42%
Thyroid receptor binding	-	0.7633	76.33%
Glucocorticoid receptor binding	-	0.6943	69.43%
Aromatase binding	-	0.8817	88.17%
PPAR gamma	-	0.9066	90.66%
Honey bee toxicity	-	0.9093	90.93%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8403	84.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	89.77%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.21%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.10%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.98%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.32%	85.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.39%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.67%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.43%	96.95%

Plants that contains it

• Gelsemium sempervirens

Cross-Links

• PubChem: 10375526
• LOTUS: LTS0224864
• wikiData: Q104998614