[(1S,4aS,7S,7aS)-4-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]oxymethyl]-7-(hydroxymethyl)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl] 3-methylbutanoate

Details

• Internal ID: 23bd91d0-a2af-4649-b60b-cdfec66f0e1b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(1S,4aS,7S,7aS)-4-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]oxymethyl]-7-(hydroxymethyl)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl] 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OC1C2C(CCC2C(=CO1)COC3C(C(C(C(O3)CO)O)O)OC(=O)C=CC4=CC=C(C=C4)O)CO
• SMILES (Isomeric): CC(C)CC(=O)O[C@H]1[C@@H]2[C@H](CC[C@@H]2C(=CO1)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)/C=C/C4=CC=C(C=C4)O)CO
• InChI: InChI=1S/C30H40O12/c1-16(2)11-24(35)42-29-25-18(12-31)6-9-21(25)19(14-38-29)15-39-30-28(27(37)26(36)22(13-32)40-30)41-23(34)10-5-17-3-7-20(33)8-4-17/h3-5,7-8,10,14,16,18,21-22,25-33,36-37H,6,9,11-13,15H2,1-2H3/b10-5+/t18-,21-,22-,25-,26-,27+,28-,29+,30-/m1/s1
• InChI Key: SSHSXBTZJKLHPW-QWOPETRYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₀O₁₂
• Molecular Weight: 592.60 g/mol
• Exact Mass: 592.25197671 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.24
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6955	69.55%
Caco-2	-	0.8659	86.59%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.8461	84.61%
OATP2B1 inhibitior	-	0.8629	86.29%
OATP1B1 inhibitior	+	0.8005	80.05%
OATP1B3 inhibitior	+	0.9062	90.62%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7421	74.21%
P-glycoprotein inhibitior	-	0.4721	47.21%
P-glycoprotein substrate	+	0.5070	50.70%
CYP3A4 substrate	+	0.6667	66.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8731	87.31%
CYP3A4 inhibition	-	0.8384	83.84%
CYP2C9 inhibition	-	0.8260	82.60%
CYP2C19 inhibition	-	0.7400	74.00%
CYP2D6 inhibition	-	0.8285	82.85%
CYP1A2 inhibition	-	0.6676	66.76%
CYP2C8 inhibition	+	0.6485	64.85%
CYP inhibitory promiscuity	-	0.8025	80.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6589	65.89%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9336	93.36%
Skin irritation	-	0.7851	78.51%
Skin corrosion	-	0.9530	95.30%
Ames mutagenesis	-	0.5940	59.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.6668	66.68%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6574	65.74%
skin sensitisation	-	0.8622	86.22%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.8561	85.61%
Acute Oral Toxicity (c)	III	0.5364	53.64%
Estrogen receptor binding	+	0.7299	72.99%
Androgen receptor binding	+	0.7571	75.71%
Thyroid receptor binding	-	0.6061	60.61%
Glucocorticoid receptor binding	+	0.5421	54.21%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5864	58.64%
Honey bee toxicity	-	0.7758	77.58%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9843	98.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.69%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.37%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	97.76%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.69%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.38%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.69%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.53%	89.00%
CHEMBL2581	P07339	Cathepsin D	92.31%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.68%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.47%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.33%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.41%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.55%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	88.17%	92.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.64%	86.92%
CHEMBL206	P03372	Estrogen receptor alpha	87.33%	97.64%
CHEMBL3401	O75469	Pregnane X receptor	85.65%	94.73%
CHEMBL242	Q92731	Estrogen receptor beta	85.36%	98.35%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	83.59%	94.23%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.18%	89.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.28%	95.89%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.10%	85.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.14%	94.80%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.11%	100.00%

Plants that contains it

• Phyllosma capensis
• Proustia ilicifolia
• Viburnum prunifolium

Cross-Links

• PubChem: 93473163
• NPASS: NPC52187
• LOTUS: LTS0085301
• wikiData: Q105259666