(2'R,3R,3aS,5R,7S,7aS)-3,5',7-trihydroxy-2',3,7-trimethyl-4'-[(2S)-2-methylbutanoyl]-2'-(3-methylbut-2-enyl)spiro[1,2,3a,4,6,7a-hexahydroindene-5,6'-cyclohex-4-ene]-1',3'-dione

Details

• Internal ID: e90c18cb-de71-4ab9-ac0c-e657df30c5d0
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Cyclic ketones > Cyclohexenones
• IUPAC Name: (2'R,3R,3aS,5R,7S,7aS)-3,5',7-trihydroxy-2',3,7-trimethyl-4'-[(2S)-2-methylbutanoyl]-2'-(3-methylbut-2-enyl)spiro[1,2,3a,4,6,7a-hexahydroindene-5,6'-cyclohex-4-ene]-1',3'-dione
• SMILES (Canonical): CCC(C)C(=O)C1=C(C2(CC3C(CCC3(C)O)C(C2)(C)O)C(=O)C(C1=O)(C)CC=C(C)C)O
• SMILES (Isomeric): CC[C@H](C)C(=O)C1=C([C@]2(C[C@H]3[C@H](CC[C@@]3(C)O)[C@@](C2)(C)O)C(=O)[C@@](C1=O)(C)CC=C(C)C)O
• InChI: InChI=1S/C27H40O6/c1-8-16(4)20(28)19-21(29)24(5,11-9-15(2)3)23(31)27(22(19)30)13-18-17(26(7,33)14-27)10-12-25(18,6)32/h9,16-18,30,32-33H,8,10-14H2,1-7H3/t16-,17-,18-,24-,25+,26-,27+/m0/s1
• InChI Key: QCZFZWDBZKCYMB-SZCQCBDQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₆
• Molecular Weight: 460.60 g/mol
• Exact Mass: 460.28248899 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.24
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9971	99.71%
Caco-2	+	0.5203	52.03%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7605	76.05%
OATP2B1 inhibitior	-	0.7169	71.69%
OATP1B1 inhibitior	+	0.8327	83.27%
OATP1B3 inhibitior	+	0.9216	92.16%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.8722	87.22%
P-glycoprotein inhibitior	-	0.6340	63.40%
P-glycoprotein substrate	+	0.5066	50.66%
CYP3A4 substrate	+	0.6455	64.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8852	88.52%
CYP3A4 inhibition	-	0.6613	66.13%
CYP2C9 inhibition	-	0.8853	88.53%
CYP2C19 inhibition	-	0.9008	90.08%
CYP2D6 inhibition	-	0.9488	94.88%
CYP1A2 inhibition	-	0.9506	95.06%
CYP2C8 inhibition	-	0.6660	66.60%
CYP inhibitory promiscuity	-	0.7721	77.21%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6230	62.30%
Eye corrosion	-	0.9950	99.50%
Eye irritation	-	0.8887	88.87%
Skin irritation	+	0.6450	64.50%
Skin corrosion	-	0.9470	94.70%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6511	65.11%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.6054	60.54%
skin sensitisation	-	0.6967	69.67%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.7059	70.59%
Acute Oral Toxicity (c)	I	0.6388	63.88%
Estrogen receptor binding	+	0.6453	64.53%
Androgen receptor binding	+	0.6533	65.33%
Thyroid receptor binding	+	0.5352	53.52%
Glucocorticoid receptor binding	+	0.7386	73.86%
Aromatase binding	+	0.6998	69.98%
PPAR gamma	+	0.7199	71.99%
Honey bee toxicity	-	0.8633	86.33%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9969	99.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.56%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.23%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	96.51%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.25%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.49%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	92.93%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.86%	100.00%
CHEMBL2581	P07339	Cathepsin D	88.78%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.28%	96.61%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.90%	89.34%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	86.73%	83.57%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.28%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.73%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.35%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.04%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.36%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	82.09%	91.19%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.81%	97.50%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.37%	85.30%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.12%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.47%	99.23%
CHEMBL236	P41143	Delta opioid receptor	80.16%	99.35%

Plants that contains it

• Hypericum monogynum

Cross-Links

• PubChem: 162945957
• LOTUS: LTS0080991
• wikiData: Q105218672