(1R,2R,3S,4S,5R,9S,10S,13R,14R)-2,3-dihydroxy-14-(hydroxymethyl)-5,9-dimethyl-14-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid

Details

• Internal ID: 4a6d11b9-873b-44af-95fc-3ecbc6577517
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (1R,2R,3S,4S,5R,9S,10S,13R,14R)-2,3-dihydroxy-14-(hydroxymethyl)-5,9-dimethyl-14-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• SMILES (Canonical): CC12CCCC(C1C(C(C34C2CCC(C3)C(C4)(CO)OC5C(C(C(C(O5)CO)O)O)O)O)O)(C)C(=O)O
• SMILES (Isomeric): C[C@@]12CCC[C@@]([C@H]1[C@@H]([C@@H]([C@]34[C@H]2CC[C@H](C3)[C@](C4)(CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)(C)C(=O)O
• InChI: InChI=1S/C26H42O11/c1-23-6-3-7-24(2,22(34)35)19(23)18(32)20(33)25-8-12(4-5-14(23)25)26(10-25,11-28)37-21-17(31)16(30)15(29)13(9-27)36-21/h12-21,27-33H,3-11H2,1-2H3,(H,34,35)/t12-,13-,14+,15-,16+,17-,18+,19+,20+,21+,23+,24-,25-,26+/m1/s1
• InChI Key: QUCGBWQRLWOVBR-WSNGDQLASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₂O₁₁
• Molecular Weight: 530.60 g/mol
• Exact Mass: 530.27271215 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.03
• H-Bond Acceptor: 10
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4928	49.28%
Caco-2	-	0.8662	86.62%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7325	73.25%
OATP2B1 inhibitior	-	0.5803	58.03%
OATP1B1 inhibitior	+	0.8404	84.04%
OATP1B3 inhibitior	+	0.9410	94.10%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9205	92.05%
P-glycoprotein inhibitior	-	0.6254	62.54%
P-glycoprotein substrate	-	0.7436	74.36%
CYP3A4 substrate	+	0.6696	66.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8706	87.06%
CYP3A4 inhibition	-	0.9397	93.97%
CYP2C9 inhibition	-	0.8742	87.42%
CYP2C19 inhibition	-	0.7944	79.44%
CYP2D6 inhibition	-	0.9551	95.51%
CYP1A2 inhibition	-	0.8420	84.20%
CYP2C8 inhibition	+	0.4682	46.82%
CYP inhibitory promiscuity	-	0.9482	94.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7358	73.58%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9436	94.36%
Skin irritation	-	0.7237	72.37%
Skin corrosion	-	0.9517	95.17%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6680	66.80%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.7598	75.98%
skin sensitisation	-	0.9387	93.87%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7667	76.67%
Acute Oral Toxicity (c)	I	0.3985	39.85%
Estrogen receptor binding	+	0.6150	61.50%
Androgen receptor binding	+	0.6549	65.49%
Thyroid receptor binding	+	0.5405	54.05%
Glucocorticoid receptor binding	+	0.5399	53.99%
Aromatase binding	+	0.7166	71.66%
PPAR gamma	+	0.5381	53.81%
Honey bee toxicity	-	0.8257	82.57%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6450	64.50%
Fish aquatic toxicity	+	0.8859	88.59%

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	97.44%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.89%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.48%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	90.88%	90.17%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.00%	96.38%
CHEMBL5255	O00206	Toll-like receptor 4	87.14%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.05%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.10%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.65%	96.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.98%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.45%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.36%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.07%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.59%	94.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.26%	95.83%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.85%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.01%	86.33%
CHEMBL237	P41145	Kappa opioid receptor	80.00%	98.10%

Plants that contains it

• Ipomoea nil

Cross-Links

• PubChem: 44179026
• LOTUS: LTS0272680
• wikiData: Q105228073