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

Details

• Internal ID: d1ec0908-46ef-495a-8a03-808ddc9d8315
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Monocyclic monoterpenoids
• IUPAC Name: (6R)-3,5-dihydroxy-4-[[(1R,2S,5S)-2-hydroxy-2-methyl-5-prop-1-en-2-ylcyclopentyl]methyl]-6-methyl-2-[(2R)-2-methylbutanoyl]-6-(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
• SMILES (Canonical): CCC(C)C(=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@@H](C)C(=O)C1=C(C(=C([C@@](C1=O)(C)CC=C(C)C)O)C[C@@H]2[C@H](CC[C@]2(C)O)C(=C)C)O
• InChI: InChI=1S/C27H40O5/c1-9-17(6)22(28)21-23(29)19(14-20-18(16(4)5)11-13-27(20,8)32)24(30)26(7,25(21)31)12-10-15(2)3/h10,17-18,20,29-30,32H,4,9,11-14H2,1-3,5-8H3/t17-,18-,20-,26-,27+/m1/s1
• InChI Key: SEHZNEFMBPPMQP-LQVOSMOHSA-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: 5.60
• 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	+	0.9830	98.30%
Caco-2	+	0.5539	55.39%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6988	69.88%
OATP2B1 inhibitior	-	0.7142	71.42%
OATP1B1 inhibitior	+	0.8533	85.33%
OATP1B3 inhibitior	+	0.8855	88.55%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.8640	86.40%
P-glycoprotein inhibitior	-	0.5600	56.00%
P-glycoprotein substrate	+	0.5465	54.65%
CYP3A4 substrate	+	0.6380	63.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8885	88.85%
CYP3A4 inhibition	-	0.6381	63.81%
CYP2C9 inhibition	-	0.7682	76.82%
CYP2C19 inhibition	-	0.7911	79.11%
CYP2D6 inhibition	-	0.9046	90.46%
CYP1A2 inhibition	-	0.9266	92.66%
CYP2C8 inhibition	-	0.6086	60.86%
CYP inhibitory promiscuity	-	0.8284	82.84%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6838	68.38%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.7767	77.67%
Skin irritation	+	0.5050	50.50%
Skin corrosion	-	0.9466	94.66%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4167	41.67%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.5076	50.76%
skin sensitisation	-	0.6532	65.32%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6659	66.59%
Acute Oral Toxicity (c)	II	0.4282	42.82%
Estrogen receptor binding	+	0.6634	66.34%
Androgen receptor binding	+	0.6093	60.93%
Thyroid receptor binding	+	0.5636	56.36%
Glucocorticoid receptor binding	+	0.7918	79.18%
Aromatase binding	+	0.6765	67.65%
PPAR gamma	+	0.6951	69.51%
Honey bee toxicity	-	0.8233	82.33%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9960	99.60%

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	97.76%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.83%	83.82%
CHEMBL2581	P07339	Cathepsin D	95.68%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.88%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.86%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	92.97%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.31%	96.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.73%	91.24%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.73%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.05%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.68%	89.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.18%	96.47%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.87%	92.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.16%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.66%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.21%	97.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.07%	89.34%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.78%	93.04%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.78%	91.07%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.26%	93.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.22%	92.88%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.14%	97.50%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.14%	93.03%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.58%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.15%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.00%	94.33%

Plants that contains it

• Hypericum monogynum

Cross-Links

• PubChem: 163022750
• LOTUS: LTS0190130
• wikiData: Q105251199