Hirsutenol A

Details

• Internal ID: 4016fb67-4d38-4911-8eb5-4db446a27eb7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Triquinane sesquiterpenoids > Linear triquinanes
• IUPAC Name: (3R,3aS,4R,7aS)-4-hydroxy-3,3a,5,5-tetramethyl-3,4,7,7a-tetrahydro-1H-cyclopenta[a]pentalene-2,6-dione
• SMILES (Canonical): CC1C(=O)CC2C1(C3=C(C2)C(=O)C(C3O)(C)C)C
• SMILES (Isomeric): C[C@H]1C(=O)C[C@H]2[C@@]1(C3=C(C2)C(=O)C([C@@H]3O)(C)C)C
• InChI: InChI=1S/C15H20O3/c1-7-10(16)6-8-5-9-11(15(7,8)4)13(18)14(2,3)12(9)17/h7-8,13,18H,5-6H2,1-4H3/t7-,8-,13+,15+/m0/s1
• InChI Key: JDNHHSVZZOCUOM-WCBQKTFOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.89
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• (3R,3aS,4R,7aS)-4-hydroxy-3,3a,5,5-tetramethyl-3,4,7,7a-tetrahydro-1H-cyclopenta[a]pentalene-2,6-dione
• (3R,3aS,4R,7aS)-4-hydroxy-3,3a,5,5-tetramethyl-3,4,7,7a-tetrahydro-1H-cyclopenta(a)pentalene-2,6-dione
• RefChem:146492
• 440121-27-7
• CHEBI:219468

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9955	99.55%
Caco-2	+	0.6618	66.18%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7427	74.27%
OATP2B1 inhibitior	-	0.8529	85.29%
OATP1B1 inhibitior	+	0.9072	90.72%
OATP1B3 inhibitior	+	0.9586	95.86%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8935	89.35%
P-glycoprotein inhibitior	-	0.9277	92.77%
P-glycoprotein substrate	-	0.7911	79.11%
CYP3A4 substrate	+	0.5333	53.33%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.8653	86.53%
CYP3A4 inhibition	-	0.8703	87.03%
CYP2C9 inhibition	-	0.8205	82.05%
CYP2C19 inhibition	-	0.8412	84.12%
CYP2D6 inhibition	-	0.9242	92.42%
CYP1A2 inhibition	-	0.7261	72.61%
CYP2C8 inhibition	-	0.9396	93.96%
CYP inhibitory promiscuity	-	0.8653	86.53%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.4790	47.90%
Eye corrosion	-	0.9635	96.35%
Eye irritation	-	0.5133	51.33%
Skin irritation	+	0.6521	65.21%
Skin corrosion	-	0.8339	83.39%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5795	57.95%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.6461	64.61%
skin sensitisation	+	0.5342	53.42%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.7362	73.62%
Acute Oral Toxicity (c)	III	0.4452	44.52%
Estrogen receptor binding	+	0.6354	63.54%
Androgen receptor binding	-	0.6295	62.95%
Thyroid receptor binding	+	0.5429	54.29%
Glucocorticoid receptor binding	-	0.5963	59.63%
Aromatase binding	-	0.6657	66.57%
PPAR gamma	-	0.6105	61.05%
Honey bee toxicity	-	0.8299	82.99%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9103	91.03%

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	91.50%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.40%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.52%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.41%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	84.27%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.15%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.80%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.57%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.66%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.02%	90.71%

Plants that contains it

• Pachysandra procumbens

Cross-Links

• PubChem: 636776
• NPASS: NPC49140
• LOTUS: LTS0126588
• wikiData: Q77503025