3,5-Dihydroxy-4-[(2-hydroxy-2-methyl-5-prop-1-en-2-ylcyclopentyl)methyl]-6-methyl-2-(3-methylbutanoyl)-6-(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one

Details

• Internal ID: 07a631ce-b48e-440b-a34a-70cf781bc1db
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Monocyclic monoterpenoids
• IUPAC Name: 3,5-dihydroxy-4-[(2-hydroxy-2-methyl-5-prop-1-en-2-ylcyclopentyl)methyl]-6-methyl-2-(3-methylbutanoyl)-6-(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
• SMILES (Canonical): CC(C)CC(=O)C1=C(C(=C(C(C1=O)(C)CC=C(C)C)O)CC2C(CCC2(C)O)C(=C)C)O
• SMILES (Isomeric): CC(C)CC(=O)C1=C(C(=C(C(C1=O)(C)CC=C(C)C)O)CC2C(CCC2(C)O)C(=C)C)O
• InChI: InChI=1S/C27H40O5/c1-15(2)9-11-26(7)24(30)19(14-20-18(17(5)6)10-12-27(20,8)32)23(29)22(25(26)31)21(28)13-16(3)4/h9,16,18,20,29-30,32H,5,10-14H2,1-4,6-8H3
• InChI Key: SERKCRYNKNGQLQ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₅
• Molecular Weight: 444.60 g/mol
• Exact Mass: 444.28757437 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 5.91
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	-	0.5322	53.22%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7472	74.72%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.8619	86.19%
OATP1B3 inhibitior	+	0.8395	83.95%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.7739	77.39%
P-glycoprotein inhibitior	-	0.5856	58.56%
P-glycoprotein substrate	+	0.5604	56.04%
CYP3A4 substrate	+	0.6429	64.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8885	88.85%
CYP3A4 inhibition	-	0.7769	77.69%
CYP2C9 inhibition	-	0.7778	77.78%
CYP2C19 inhibition	-	0.8118	81.18%
CYP2D6 inhibition	-	0.9299	92.99%
CYP1A2 inhibition	-	0.9203	92.03%
CYP2C8 inhibition	-	0.5933	59.33%
CYP inhibitory promiscuity	-	0.8969	89.69%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9228	92.28%
Carcinogenicity (trinary)	Non-required	0.6906	69.06%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.7815	78.15%
Skin irritation	+	0.5317	53.17%
Skin corrosion	-	0.9492	94.92%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3681	36.81%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.6201	62.01%
skin sensitisation	-	0.6335	63.35%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.7504	75.04%
Acute Oral Toxicity (c)	I	0.4677	46.77%
Estrogen receptor binding	+	0.6610	66.10%
Androgen receptor binding	+	0.5590	55.90%
Thyroid receptor binding	+	0.5749	57.49%
Glucocorticoid receptor binding	+	0.7779	77.79%
Aromatase binding	+	0.7037	70.37%
PPAR gamma	+	0.7154	71.54%
Honey bee toxicity	-	0.7959	79.59%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9938	99.38%

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	97.64%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.12%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	95.70%	90.17%
CHEMBL2581	P07339	Cathepsin D	95.45%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.49%	97.25%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	92.50%	91.24%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.39%	96.47%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.09%	96.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.17%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.76%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.84%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.52%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.30%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.93%	92.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.91%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.54%	99.23%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.18%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.88%	91.07%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	81.60%	96.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.02%	93.00%
CHEMBL226	P30542	Adenosine A1 receptor	80.87%	95.93%
CHEMBL299	P17252	Protein kinase C alpha	80.77%	98.03%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.20%	94.33%

Plants that contains it

• Hypericum calycinum

Cross-Links

• PubChem: 360845
• LOTUS: LTS0042353
• wikiData: Q105251451