(E,6S)-6-[(2R,5S)-5-[(2R,5R)-5-[(2S,5R)-5-[(E,2S)-6-hydroperoxy-2-hydroxy-6-methylhept-4-en-2-yl]-2-methyloxolan-2-yl]oxolan-2-yl]-5-methyloxolan-2-yl]-2-methylhept-3-ene-2,6-diol

Details

• Internal ID: a075c3f1-d40a-4976-9788-d5cfa83d1479
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (E,6S)-6-[(2R,5S)-5-[(2R,5R)-5-[(2S,5R)-5-[(E,2S)-6-hydroperoxy-2-hydroxy-6-methylhept-4-en-2-yl]-2-methyloxolan-2-yl]oxolan-2-yl]-5-methyloxolan-2-yl]-2-methylhept-3-ene-2,6-diol
• SMILES (Canonical): CC1(CCC(O1)C(C)(CC=CC(C)(C)O)O)C2CCC(O2)C3(CCC(O3)C(C)(CC=CC(C)(C)OO)O)C
• SMILES (Isomeric): C[C@]1(CC[C@@H](O1)[C@](C)(C/C=C/C(C)(C)O)O)[C@H]2CC[C@@H](O2)[C@@]3(CC[C@@H](O3)[C@](C)(C/C=C/C(C)(C)OO)O)C
• InChI: InChI=1S/C30H52O8/c1-25(2,31)15-9-17-27(5,32)21-13-19-29(7,36-21)23-11-12-24(35-23)30(8)20-14-22(37-30)28(6,33)18-10-16-26(3,4)38-34/h9-10,15-16,21-24,31-34H,11-14,17-20H2,1-8H3/b15-9+,16-10+/t21-,22-,23-,24-,27+,28+,29+,30+/m1/s1
• InChI Key: QLFRXAKUUDRERJ-BOWISWASSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₂O₈
• Molecular Weight: 540.70 g/mol
• Exact Mass: 540.36621861 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 4.84
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 11

Synonyms

• CHEMBL64580
• (2S)-2-[(2S,2'R,2''S,5R,5'R,5''R)-2,2''-Dimethyl-5''-[(1S)-1-hydroxy-1,5-dimethyl-5-hydroperoxy-3-hexenyl]dodecahydro[2,2':5',2''-terfuran]-5-yl]-6-methyl-4-heptene-2,6-diol
• (alphaS,alpha'S,2S,2'R,2''S,5R,5'R,5''R)-alpha-[(E)-4-Methyl-4-hydroperoxy-2-pentenyl]-alpha'-(4-hydroxy-4-methyl-2-pentenyl)-alpha,alpha',2,2''-tetramethyl-2,2':5',2''-teroxolane-5,5''-dimethanol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9383	93.83%
Caco-2	-	0.7692	76.92%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6739	67.39%
OATP2B1 inhibitior	-	0.7146	71.46%
OATP1B1 inhibitior	+	0.8922	89.22%
OATP1B3 inhibitior	+	0.9179	91.79%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7294	72.94%
P-glycoprotein inhibitior	+	0.7035	70.35%
P-glycoprotein substrate	-	0.8289	82.89%
CYP3A4 substrate	+	0.6599	65.99%
CYP2C9 substrate	-	0.6117	61.17%
CYP2D6 substrate	-	0.7776	77.76%
CYP3A4 inhibition	-	0.8468	84.68%
CYP2C9 inhibition	-	0.7581	75.81%
CYP2C19 inhibition	-	0.7348	73.48%
CYP2D6 inhibition	-	0.9141	91.41%
CYP1A2 inhibition	-	0.7618	76.18%
CYP2C8 inhibition	-	0.6197	61.97%
CYP inhibitory promiscuity	-	0.7208	72.08%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7328	73.28%
Carcinogenicity (trinary)	Non-required	0.6030	60.30%
Eye corrosion	-	0.9498	94.98%
Eye irritation	-	0.9317	93.17%
Skin irritation	-	0.6576	65.76%
Skin corrosion	-	0.9046	90.46%
Ames mutagenesis	+	0.5263	52.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7274	72.74%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.6024	60.24%
skin sensitisation	-	0.6417	64.17%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.4846	48.46%
Acute Oral Toxicity (c)	III	0.5581	55.81%
Estrogen receptor binding	+	0.7550	75.50%
Androgen receptor binding	+	0.5420	54.20%
Thyroid receptor binding	+	0.6492	64.92%
Glucocorticoid receptor binding	+	0.7633	76.33%
Aromatase binding	+	0.7100	71.00%
PPAR gamma	+	0.6465	64.65%
Honey bee toxicity	-	0.7535	75.35%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8959	89.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	98.17%	89.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.13%	96.09%
CHEMBL233	P35372	Mu opioid receptor	93.42%	97.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.42%	97.25%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	87.36%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.98%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.87%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.45%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.41%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.50%	94.45%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.50%	97.28%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.15%	95.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.35%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	80.04%	95.93%

Plants that contains it

• Aralidium pinnatifidum
• Bersama swinnyi
• Blainvillea acmella
• Euphorbia resinifera
• Eurycoma longifolia
• Geigeria schinzii
• Goniothalamus undulatus
• Gymnospermium kiangnanensis
• Helichrysum sutherlandii
• Hemionitis marantae
• Lophocereus marginatus
• Nemuaron vieillardii
• Ophryosporus charua
• Oreomecon radicata
• Pachycereus pringlei
• Picea laxa
• Prosopis kuntzei
• Pteris leptophylla
• Stenocereus thurberi
• Vitex negundo

Cross-Links

• PubChem: 10896840
• NPASS: NPC137345
• LOTUS: LTS0221732
• wikiData: Q105223551