15-Nor-guaianolide

Details

• Internal ID: 13fa7cb2-e1ab-450b-8a9f-9e76553e6f7c
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3S,3aR,4S,6aR,9aS,9bR)-4-hydroxy-3-methyl-6-methylidene-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione
• SMILES (Canonical): CC1C2C(CC(=C)C3CC(=O)CC3C2OC1=O)O
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](CC(=C)[C@@H]3CC(=O)C[C@@H]3[C@H]2OC1=O)O
• InChI: InChI=1S/C14H18O4/c1-6-3-11(16)12-7(2)14(17)18-13(12)10-5-8(15)4-9(6)10/h7,9-13,16H,1,3-5H2,2H3/t7-,9-,10-,11-,12+,13+/m0/s1
• InChI Key: OFCPFJBHYYGYRX-ZNNZHFKNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.29 g/mol
• Exact Mass: 250.12050905 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.08
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• CHEMBL1802040

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9865	98.65%
Caco-2	+	0.5944	59.44%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5871	58.71%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8454	84.54%
OATP1B3 inhibitior	+	0.9517	95.17%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9350	93.50%
P-glycoprotein inhibitior	-	0.9241	92.41%
P-glycoprotein substrate	-	0.8029	80.29%
CYP3A4 substrate	+	0.5423	54.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8352	83.52%
CYP3A4 inhibition	-	0.8249	82.49%
CYP2C9 inhibition	-	0.9135	91.35%
CYP2C19 inhibition	-	0.8663	86.63%
CYP2D6 inhibition	-	0.9588	95.88%
CYP1A2 inhibition	-	0.7683	76.83%
CYP2C8 inhibition	-	0.9310	93.10%
CYP inhibitory promiscuity	-	0.9654	96.54%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9325	93.25%
Carcinogenicity (trinary)	Non-required	0.5457	54.57%
Eye corrosion	-	0.9155	91.55%
Eye irritation	-	0.5292	52.92%
Skin irritation	-	0.5502	55.02%
Skin corrosion	-	0.8854	88.54%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7220	72.20%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.6837	68.37%
skin sensitisation	-	0.7322	73.22%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5938	59.38%
Acute Oral Toxicity (c)	III	0.3950	39.50%
Estrogen receptor binding	-	0.7179	71.79%
Androgen receptor binding	-	0.5524	55.24%
Thyroid receptor binding	-	0.6032	60.32%
Glucocorticoid receptor binding	-	0.5257	52.57%
Aromatase binding	-	0.7630	76.30%
PPAR gamma	-	0.8018	80.18%
Honey bee toxicity	-	0.7611	76.11%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9629	96.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.17%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.25%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	90.83%	91.49%
CHEMBL2581	P07339	Cathepsin D	90.06%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.94%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.52%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.33%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.18%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.91%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.95%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.77%	100.00%

Plants that contains it

• Centaurea deflexa

Cross-Links

• PubChem: 53328018
• LOTUS: LTS0049552
• wikiData: Q105203944