(1S,2R,5R,7S,10R,11R,15S,18S,20R,22S)-7-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-18-(4-methoxybenzoyl)oxy-2,6,6,10,17,17-hexamethylhexacyclo[12.9.0.01,22.02,11.05,10.015,20]tricos-13-ene-20-carboxylic acid

Details

• Internal ID: 09d0aacb-bc1d-4f71-9f73-7c38100b4083
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1S,2R,5R,7S,10R,11R,15S,18S,20R,22S)-7-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-18-(4-methoxybenzoyl)oxy-2,6,6,10,17,17-hexamethylhexacyclo[12.9.0.01,22.02,11.05,10.015,20]tricos-13-ene-20-carboxylic acid
• SMILES (Canonical): CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C36CC6CC2(CC1OC(=O)C7=CC=C(C=C7)OC)C(=O)O)C)(C)C)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(CO9)OC1C(C(C(CO1)O)O)O)O)O)C)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]35C[C@H]5C[C@@]6([C@H]4CC([C@H](C6)OC(=O)C7=CC=C(C=C7)OC)(C)C)C(=O)O)C)(C)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O
• InChI: InChI=1S/C54H78O19/c1-49(2)20-29-28-12-13-34-51(5)16-15-35(72-47-43(40(60)38(58)31(22-55)69-47)73-46-42(62)39(59)32(24-68-46)70-45-41(61)37(57)30(56)23-67-45)50(3,4)33(51)14-17-52(34,6)54(28)19-26(54)18-53(29,48(64)65)21-36(49)71-44(63)25-8-10-27(66-7)11-9-25/h8-12,26,29-43,45-47,55-62H,13-24H2,1-7H3,(H,64,65)/t26-,29+,30-,31-,32-,33+,34-,35+,36+,37+,38-,39+,40+,41-,42-,43-,45+,46+,47+,51+,52-,53-,54-/m1/s1
• InChI Key: NAYUDDIXRCZONZ-PLORLKPISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₇₈O₁₉
• Molecular Weight: 1031.20 g/mol
• Exact Mass: 1030.51373025 g/mol
• Topological Polar Surface Area (TPSA): 290.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.44
• H-Bond Acceptor: 18
• H-Bond Donor: 9
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8573	85.73%
Caco-2	-	0.8675	86.75%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7390	73.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7603	76.03%
OATP1B3 inhibitior	+	0.7975	79.75%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9814	98.14%
P-glycoprotein inhibitior	+	0.7475	74.75%
P-glycoprotein substrate	+	0.6075	60.75%
CYP3A4 substrate	+	0.7532	75.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8664	86.64%
CYP3A4 inhibition	-	0.7256	72.56%
CYP2C9 inhibition	-	0.7221	72.21%
CYP2C19 inhibition	-	0.7710	77.10%
CYP2D6 inhibition	-	0.9200	92.00%
CYP1A2 inhibition	-	0.7707	77.07%
CYP2C8 inhibition	+	0.8203	82.03%
CYP inhibitory promiscuity	-	0.9504	95.04%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6076	60.76%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9003	90.03%
Skin irritation	-	0.7114	71.14%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7906	79.06%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.7643	76.43%
skin sensitisation	-	0.8676	86.76%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7931	79.31%
Acute Oral Toxicity (c)	III	0.5234	52.34%
Estrogen receptor binding	+	0.7598	75.98%
Androgen receptor binding	+	0.7573	75.73%
Thyroid receptor binding	+	0.5950	59.50%
Glucocorticoid receptor binding	+	0.7604	76.04%
Aromatase binding	+	0.6492	64.92%
PPAR gamma	+	0.8137	81.37%
Honey bee toxicity	-	0.6613	66.13%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9791	97.91%

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	98.02%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	97.86%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.68%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.07%	97.09%
CHEMBL4208	P20618	Proteasome component C5	95.01%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.86%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.90%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.88%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.53%	96.77%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.31%	99.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.26%	91.07%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.20%	95.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.02%	92.62%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.79%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.70%	95.56%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.54%	95.83%
CHEMBL340	P08684	Cytochrome P450 3A4	84.16%	91.19%
CHEMBL5028	O14672	ADAM10	83.74%	97.50%
CHEMBL2581	P07339	Cathepsin D	83.60%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.59%	100.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.49%	97.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.52%	97.14%

Plants that contains it

• Verbesina virginica

Cross-Links

• PubChem: 44179859
• LOTUS: LTS0249100
• wikiData: Q105176641