Acurea

Details

• Internal ID: 8dd3625a-89c3-43f0-93f4-76f7a35956d1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: 4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione
• SMILES (Canonical): CC(C)C(=O)C12C(=O)C(=C(C(C1=O)(CC(C2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)O)CC=C(C)C
• SMILES (Isomeric): CC(C)C(=O)C12C(=O)C(=C(C(C1=O)(CC(C2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)O)CC=C(C)C
• InChI: InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3
• InChI Key: KGSZHKRKHXOAMG-UHFFFAOYSA-N
• Popularity: 16 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₂O₄
• Molecular Weight: 536.80 g/mol
• Exact Mass: 536.38656014 g/mol
• Topological Polar Surface Area (TPSA): 71.40 Ų
• XlogP: 9.60
• Atomic LogP (AlogP): 8.99
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 11

Synonyms

• C35-H52-O4
• D0Q7SP
• SCHEMBL8168239
• KGSZHKRKHXOAMG-UHFFFAOYSA-N
• FT-0627168
• Q27461275
• 4-Hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9964	99.64%
Caco-2	+	0.5420	54.20%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8231	82.31%
OATP2B1 inhibitior	-	0.8516	85.16%
OATP1B1 inhibitior	+	0.8747	87.47%
OATP1B3 inhibitior	+	0.8129	81.29%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9361	93.61%
P-glycoprotein inhibitior	-	0.7326	73.26%
P-glycoprotein substrate	-	0.5295	52.95%
CYP3A4 substrate	+	0.6255	62.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8725	87.25%
CYP3A4 inhibition	-	0.7651	76.51%
CYP2C9 inhibition	-	0.7842	78.42%
CYP2C19 inhibition	-	0.9081	90.81%
CYP2D6 inhibition	-	0.9537	95.37%
CYP1A2 inhibition	-	0.8671	86.71%
CYP2C8 inhibition	-	0.7991	79.91%
CYP inhibitory promiscuity	-	0.8690	86.90%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6387	63.87%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.8916	89.16%
Skin irritation	-	0.5190	51.90%
Skin corrosion	-	0.9634	96.34%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7497	74.97%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.8679	86.79%
skin sensitisation	+	0.5304	53.04%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.7090	70.90%
Acute Oral Toxicity (c)	III	0.4938	49.38%
Estrogen receptor binding	+	0.7091	70.91%
Androgen receptor binding	+	0.6053	60.53%
Thyroid receptor binding	+	0.6975	69.75%
Glucocorticoid receptor binding	+	0.6946	69.46%
Aromatase binding	+	0.7160	71.60%
PPAR gamma	+	0.7419	74.19%
Honey bee toxicity	-	0.8336	83.36%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3401	O75469	Pregnane X receptor	27 nM	Ki	via Super-PRED
CHEMBL5658	O14684	Prostaglandin E synthase	30 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.98%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	98.67%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.78%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.02%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.85%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.67%	97.25%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.30%	89.34%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.95%	97.09%
CHEMBL284	P27487	Dipeptidyl peptidase IV	82.95%	95.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.56%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.32%	95.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.75%	90.08%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.31%	83.57%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.04%	90.71%

Plants that contains it

• Hypericum perforatum

Cross-Links

• PubChem: 3662
• NPASS: NPC119823
• LOTUS: LTS0083959
• wikiData: Q105140966