(2S,4S,7R,8S,9S,12R,13R,16S,18R)-7-[(E)-4-hydroperoxy-4-methylpent-2-enyl]-16-hydroxy-2,9,13,17,17-pentamethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-1(20)-ene-6,19-dione

Details

• Internal ID: 28a5cf59-8960-43f8-b0ed-94b4f6c2d1f2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,4S,7R,8S,9S,12R,13R,16S,18R)-7-[(E)-4-hydroperoxy-4-methylpent-2-enyl]-16-hydroxy-2,9,13,17,17-pentamethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-1(20)-ene-6,19-dione
• SMILES (Canonical): CC1(C(CCC2(C1C(=O)C=C3C2CCC4(C3(CC5C4C(C(=O)O5)CC=CC(C)(C)OO)C)C)C)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1C(=O)C=C3[C@@H]2CC[C@@]4([C@@]3(C[C@H]5[C@H]4[C@H](C(=O)O5)C/C=C/C(C)(C)OO)C)C)(C)C)O
• InChI: InChI=1S/C30H44O6/c1-26(2,36-34)12-8-9-17-23-21(35-25(17)33)16-30(7)19-15-20(31)24-27(3,4)22(32)11-13-28(24,5)18(19)10-14-29(23,30)6/h8,12,15,17-18,21-24,32,34H,9-11,13-14,16H2,1-7H3/b12-8+/t17-,18+,21+,22+,23-,24+,28-,29+,30-/m1/s1
• InChI Key: YDANZQNAKUJCQB-SILJCLGZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₄O₆
• Molecular Weight: 500.70 g/mol
• Exact Mass: 500.31378912 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 5.50
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	-	0.5976	59.76%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7912	79.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7968	79.68%
OATP1B3 inhibitior	+	0.8595	85.95%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6282	62.82%
BSEP inhibitior	+	0.9601	96.01%
P-glycoprotein inhibitior	+	0.7118	71.18%
P-glycoprotein substrate	-	0.5655	56.55%
CYP3A4 substrate	+	0.7263	72.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9022	90.22%
CYP3A4 inhibition	+	0.5934	59.34%
CYP2C9 inhibition	-	0.7682	76.82%
CYP2C19 inhibition	-	0.8732	87.32%
CYP2D6 inhibition	-	0.9295	92.95%
CYP1A2 inhibition	-	0.8142	81.42%
CYP2C8 inhibition	+	0.5231	52.31%
CYP inhibitory promiscuity	-	0.7776	77.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5886	58.86%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9394	93.94%
Skin irritation	-	0.5370	53.70%
Skin corrosion	-	0.9106	91.06%
Ames mutagenesis	-	0.5382	53.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.4284	42.84%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.7722	77.22%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.4663	46.63%
Acute Oral Toxicity (c)	III	0.5162	51.62%
Estrogen receptor binding	+	0.8098	80.98%
Androgen receptor binding	+	0.7392	73.92%
Thyroid receptor binding	+	0.6577	65.77%
Glucocorticoid receptor binding	+	0.8316	83.16%
Aromatase binding	+	0.7656	76.56%
PPAR gamma	+	0.6297	62.97%
Honey bee toxicity	-	0.6936	69.36%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9968	99.68%

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	96.63%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.24%	96.09%
CHEMBL204	P00734	Thrombin	95.41%	96.01%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	95.12%	94.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.23%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.08%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.71%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.98%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.86%	97.25%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	89.59%	89.34%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.51%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	89.00%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.73%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.31%	82.69%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.69%	91.07%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.11%	97.28%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.10%	95.89%
CHEMBL2581	P07339	Cathepsin D	81.82%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	81.64%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.60%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.47%	92.62%

Plants that contains it

• Melia azedarach

Cross-Links

• PubChem: 46210177
• LOTUS: LTS0269263
• wikiData: Q105346627