3b,6-Dihydroxy-3a,5,5-trimethyl-3-methylidene-4,6-dihydrocyclopenta[a]pentalen-2-one

Details

• Internal ID: aa463e4c-137a-4928-bb0f-71cb31c88569
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Triquinane sesquiterpenoids > Linear triquinanes
• IUPAC Name: 3b,6-dihydroxy-3a,5,5-trimethyl-3-methylidene-4,6-dihydrocyclopenta[a]pentalen-2-one
• SMILES (Canonical): CC1(CC2(C(=CC3=CC(=O)C(=C)C32C)C1O)O)C
• SMILES (Isomeric): CC1(CC2(C(=CC3=CC(=O)C(=C)C32C)C1O)O)C
• InChI: InChI=1S/C15H18O3/c1-8-11(16)6-9-5-10-12(17)13(2,3)7-15(10,18)14(8,9)4/h5-6,12,17-18H,1,7H2,2-4H3
• InChI Key: INXSHIYPCYEVGP-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.52
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	+	0.7729	77.29%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5545	55.45%
OATP2B1 inhibitior	-	0.8605	86.05%
OATP1B1 inhibitior	+	0.9334	93.34%
OATP1B3 inhibitior	+	0.9232	92.32%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8795	87.95%
P-glycoprotein inhibitior	-	0.9402	94.02%
P-glycoprotein substrate	-	0.8646	86.46%
CYP3A4 substrate	+	0.5378	53.78%
CYP2C9 substrate	-	0.7713	77.13%
CYP2D6 substrate	-	0.8753	87.53%
CYP3A4 inhibition	-	0.8103	81.03%
CYP2C9 inhibition	-	0.7826	78.26%
CYP2C19 inhibition	-	0.7435	74.35%
CYP2D6 inhibition	-	0.9042	90.42%
CYP1A2 inhibition	-	0.7620	76.20%
CYP2C8 inhibition	-	0.9057	90.57%
CYP inhibitory promiscuity	-	0.7581	75.81%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5244	52.44%
Eye corrosion	-	0.9750	97.50%
Eye irritation	-	0.4881	48.81%
Skin irritation	+	0.5192	51.92%
Skin corrosion	-	0.8523	85.23%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7802	78.02%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5450	54.50%
skin sensitisation	-	0.5479	54.79%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5895	58.95%
Acute Oral Toxicity (c)	III	0.3296	32.96%
Estrogen receptor binding	-	0.5728	57.28%
Androgen receptor binding	+	0.6316	63.16%
Thyroid receptor binding	+	0.6325	63.25%
Glucocorticoid receptor binding	-	0.5853	58.53%
Aromatase binding	+	0.5277	52.77%
PPAR gamma	+	0.6110	61.10%
Honey bee toxicity	-	0.9245	92.45%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9528	95.28%

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	95.11%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.80%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.16%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.82%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.54%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.38%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.58%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.54%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.65%	94.75%

Plants that contains it

• Carthamus tinctorius

Cross-Links

• PubChem: 78201177
• LOTUS: LTS0139559
• wikiData: Q105013688