(3S)-5-[[(1R,3aS,4R,5Z,9S,12aR)-4-acetyloxy-9-hydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1,2,3,4,7,8,9,11,12,12a-decahydrocyclopenta[11]annulen-6-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid

Details

• Internal ID: 114ab61b-b729-4b63-81c0-77bd9a15b0b8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (3S)-5-[[(1R,3aS,4R,5Z,9S,12aR)-4-acetyloxy-9-hydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1,2,3,4,7,8,9,11,12,12a-decahydrocyclopenta[11]annulen-6-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
• SMILES (Canonical): CC(=O)OC1C=C(CCC(C(=C)CCC2C1(CCC2C(C)(C)O)C)O)COC(=O)CC(C)(CC(=O)O)O
• SMILES (Isomeric): CC(=O)O[C@@H]1/C=C(/CC[C@@H](C(=C)CC[C@H]2[C@@]1(CC[C@H]2C(C)(C)O)C)O)\COC(=O)C[C@](C)(CC(=O)O)O
• InChI: InChI=1S/C28H44O9/c1-17-7-9-21-20(26(3,4)34)11-12-28(21,6)23(37-18(2)29)13-19(8-10-22(17)30)16-36-25(33)15-27(5,35)14-24(31)32/h13,20-23,30,34-35H,1,7-12,14-16H2,2-6H3,(H,31,32)/b19-13-/t20-,21-,22+,23-,27+,28+/m1/s1
• InChI Key: MKGUELHKGOBNJC-OGIAISHBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₄O₉
• Molecular Weight: 524.60 g/mol
• Exact Mass: 524.29853298 g/mol
• Topological Polar Surface Area (TPSA): 151.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 3.30
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9708	97.08%
Caco-2	-	0.7399	73.99%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7800	78.00%
OATP2B1 inhibitior	-	0.7156	71.56%
OATP1B1 inhibitior	+	0.8506	85.06%
OATP1B3 inhibitior	+	0.8505	85.05%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6525	65.25%
BSEP inhibitior	+	0.8908	89.08%
P-glycoprotein inhibitior	+	0.6243	62.43%
P-glycoprotein substrate	-	0.5541	55.41%
CYP3A4 substrate	+	0.7261	72.61%
CYP2C9 substrate	-	0.8176	81.76%
CYP2D6 substrate	-	0.8786	87.86%
CYP3A4 inhibition	-	0.8327	83.27%
CYP2C9 inhibition	-	0.6419	64.19%
CYP2C19 inhibition	-	0.8824	88.24%
CYP2D6 inhibition	-	0.9469	94.69%
CYP1A2 inhibition	-	0.8022	80.22%
CYP2C8 inhibition	+	0.6170	61.70%
CYP inhibitory promiscuity	-	0.9179	91.79%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6845	68.45%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9139	91.39%
Skin irritation	+	0.5131	51.31%
Skin corrosion	-	0.9564	95.64%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7554	75.54%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8375	83.75%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7500	75.00%
Acute Oral Toxicity (c)	I	0.3750	37.50%
Estrogen receptor binding	+	0.7749	77.49%
Androgen receptor binding	+	0.6132	61.32%
Thyroid receptor binding	+	0.5282	52.82%
Glucocorticoid receptor binding	+	0.7991	79.91%
Aromatase binding	+	0.7263	72.63%
PPAR gamma	+	0.6072	60.72%
Honey bee toxicity	-	0.7247	72.47%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9944	99.44%

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	96.97%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.79%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.77%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	94.11%	94.62%
CHEMBL2581	P07339	Cathepsin D	91.70%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.76%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.25%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	87.49%	90.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.47%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.97%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.30%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.08%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.92%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.50%	95.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.07%	94.08%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.73%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.66%	97.09%
CHEMBL5028	O14672	ADAM10	82.29%	97.50%

Plants that contains it

• Chrozophora plicata

Cross-Links

• PubChem: 163031412
• LOTUS: LTS0155962
• wikiData: Q105165980