(5R)-2,6,9-humulatrien-5-ol-8-one

Details

• Internal ID: 7d7c4d92-3ae0-486b-9fa2-83aad6d833f2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2E,4R,6E,10E)-4-hydroxy-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one
• SMILES (Canonical): CC1=CCC(C=CC(=O)C(=CC(C1)O)C)(C)C
• SMILES (Isomeric): C/C/1=C\CC(/C=C/C(=O)/C(=C/[C@@H](C1)O)/C)(C)C
• InChI: InChI=1S/C15H22O2/c1-11-5-7-15(3,4)8-6-14(17)12(2)10-13(16)9-11/h5-6,8,10,13,16H,7,9H2,1-4H3/b8-6+,11-5+,12-10+/t13-/m1/s1
• InChI Key: NBVYFPSAUFQMAK-XVCAIJIUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33 g/mol
• Exact Mass: 234.161979940 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• (5R)-2,6,9-humulatrien-5-ol-8-one
• BDBM50242095

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9174	91.74%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6432	64.32%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.9410	94.10%
OATP1B3 inhibitior	+	0.9696	96.96%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6156	61.56%
P-glycoprotein inhibitior	-	0.9441	94.41%
P-glycoprotein substrate	-	0.8740	87.40%
CYP3A4 substrate	+	0.5581	55.81%
CYP2C9 substrate	-	0.8151	81.51%
CYP2D6 substrate	-	0.8720	87.20%
CYP3A4 inhibition	-	0.7546	75.46%
CYP2C9 inhibition	-	0.9217	92.17%
CYP2C19 inhibition	-	0.8526	85.26%
CYP2D6 inhibition	-	0.9333	93.33%
CYP1A2 inhibition	-	0.8093	80.93%
CYP2C8 inhibition	-	0.9505	95.05%
CYP inhibitory promiscuity	-	0.9159	91.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7644	76.44%
Carcinogenicity (trinary)	Non-required	0.5654	56.54%
Eye corrosion	-	0.9403	94.03%
Eye irritation	+	0.6243	62.43%
Skin irritation	+	0.6752	67.52%
Skin corrosion	-	0.9303	93.03%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5487	54.87%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.6857	68.57%
skin sensitisation	+	0.8430	84.30%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	-	0.6000	60.00%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	+	0.8077	80.77%
Acute Oral Toxicity (c)	III	0.7576	75.76%
Estrogen receptor binding	-	0.8005	80.05%
Androgen receptor binding	-	0.8546	85.46%
Thyroid receptor binding	-	0.7715	77.15%
Glucocorticoid receptor binding	-	0.8040	80.40%
Aromatase binding	-	0.5383	53.83%
PPAR gamma	-	0.6660	66.60%
Honey bee toxicity	-	0.9161	91.61%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9221	92.21%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	35500 nM	IC50	PMID: 15270556

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.72%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	88.01%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.44%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.84%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.77%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.03%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.62%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.40%	100.00%
CHEMBL1871	P10275	Androgen Receptor	80.64%	96.43%

Plants that contains it

• Zingiber zerumbet

Cross-Links

• PubChem: 11310871
• NPASS: NPC71755
• ChEMBL: CHEMBL469850