(1S,4S,5R,8R,10S,13S,14R,17S,18R,20S)-10-[(2S,3R,4S,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-20-(hydroxymethyl)-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-2-one

Details

• Internal ID: ab54be69-8061-46ac-90bc-1e8dfb07a139
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1S,4S,5R,8R,10S,13S,14R,17S,18R,20S)-10-[(2S,3R,4S,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-20-(hydroxymethyl)-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-2-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3COC(C(C3O)OC4C(C(C(C(O4)CO)O)O)O)OC5CCC6(C(C5(C)C)CCC7(C6CCC89C7(CC(=O)C1(C8CC(CC1)(C)CO)CO9)C)C)C)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@H]3CO[C@H]([C@@H]([C@H]3O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@H]5CC[C@]6([C@H]7CC[C@@]89[C@@H]1C[C@@](CC[C@]1(CO8)C(=O)C[C@]9([C@@]7(CC[C@H]6C5(C)C)C)C)(C)CO)C)CO)O)O)O)O)O
• InChI: InChI=1S/C53H86O22/c1-23-32(58)36(62)39(65)43(69-23)75-42-38(64)34(60)25(19-55)71-46(42)72-26-20-67-45(41(35(26)61)74-44-40(66)37(63)33(59)24(18-54)70-44)73-31-10-11-49(5)27(47(31,2)3)8-12-50(6)28(49)9-13-53-29-16-48(4,21-56)14-15-52(29,22-68-53)30(57)17-51(50,53)7/h23-29,31-46,54-56,58-66H,8-22H2,1-7H3/t23-,24+,25+,26-,27-,28+,29+,31-,32-,33+,34+,35-,36+,37-,38-,39+,40+,41+,42+,43-,44-,45-,46-,48-,49+,50+,51-,52+,53-/m0/s1
• InChI Key: ZCZLLNVVNZQJPH-OATIXLRLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₆O₂₂
• Molecular Weight: 1075.20 g/mol
• Exact Mass: 1074.56107437 g/mol
• Topological Polar Surface Area (TPSA): 343.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.50
• H-Bond Acceptor: 22
• H-Bond Donor: 12
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5657	56.57%
Caco-2	-	0.8826	88.26%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7788	77.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8064	80.64%
OATP1B3 inhibitior	+	0.9214	92.14%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.6854	68.54%
P-glycoprotein inhibitior	+	0.7450	74.50%
P-glycoprotein substrate	+	0.5232	52.32%
CYP3A4 substrate	+	0.7501	75.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8546	85.46%
CYP3A4 inhibition	-	0.9523	95.23%
CYP2C9 inhibition	-	0.8384	83.84%
CYP2C19 inhibition	-	0.8391	83.91%
CYP2D6 inhibition	-	0.9523	95.23%
CYP1A2 inhibition	-	0.9014	90.14%
CYP2C8 inhibition	+	0.7071	70.71%
CYP inhibitory promiscuity	-	0.9486	94.86%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6596	65.96%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9023	90.23%
Skin irritation	-	0.7218	72.18%
Skin corrosion	-	0.9467	94.67%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7267	72.67%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.9276	92.76%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.4533	45.33%
Acute Oral Toxicity (c)	I	0.5225	52.25%
Estrogen receptor binding	+	0.8060	80.60%
Androgen receptor binding	+	0.7554	75.54%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7063	70.63%
Aromatase binding	+	0.6510	65.10%
PPAR gamma	+	0.7926	79.26%
Honey bee toxicity	-	0.5571	55.71%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9141	91.41%

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	98.27%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	92.36%	94.75%
CHEMBL2581	P07339	Cathepsin D	92.33%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	91.32%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.25%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.11%	92.94%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.88%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.73%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.36%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.66%	96.61%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.31%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.28%	97.09%
CHEMBL332	P03956	Matrix metalloproteinase-1	85.08%	94.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.62%	89.00%
CHEMBL3524	P56524	Histone deacetylase 4	84.10%	92.97%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.84%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.53%	100.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.12%	97.33%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	82.26%	89.44%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	82.23%	83.57%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.32%	93.04%
CHEMBL259	P32245	Melanocortin receptor 4	80.82%	95.38%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.48%	95.83%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.39%	89.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.17%	99.17%

Plants that contains it

• Ardisia mamillata

Cross-Links

• PubChem: 162885876
• LOTUS: LTS0245608
• wikiData: Q105371887