2-[(1R,2R,4aR,4bS,6aS,10aS,12aR)-6a-[(2S,3R,4S,5R,6R)-6-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxycarbonyl-1-(3-hydroxypropyl)-1,4a,4b,9,9-pentamethyl-3,4,5,6,7,8,10,10a,12,12a-decahydro-2H-chrysen-2-yl]prop-2-enoic acid

Details

• Internal ID: b6027111-f591-4053-a2c5-2b59ce337c2b
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: 2-[(1R,2R,4aR,4bS,6aS,10aS,12aR)-6a-[(2S,3R,4S,5R,6R)-6-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxycarbonyl-1-(3-hydroxypropyl)-1,4a,4b,9,9-pentamethyl-3,4,5,6,7,8,10,10a,12,12a-decahydro-2H-chrysen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC(C4(C)CCCO)C(=C)C(=O)O)C)C2C1)C)C(=O)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)OC7C(C(C(C(O7)CO)O)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)O)C
• SMILES (Isomeric): C[C@@]12CC[C@H]([C@]([C@H]1CC=C3[C@]2(CC[C@@]4([C@H]3CC(CC4)(C)C)C(=O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)C)(C)CCCO)C(=C)C(=O)O
• InChI: InChI=1S/C54H86O25/c1-23(44(69)70)24-10-12-53(6)31(51(24,4)11-7-17-55)9-8-25-26-18-50(2,3)13-15-54(26,16-14-52(25,53)5)49(71)79-47-41(68)42(77-45-39(66)36(63)32(59)27(19-56)73-45)35(62)30(76-47)22-72-48-43(38(65)34(61)29(21-58)75-48)78-46-40(67)37(64)33(60)28(20-57)74-46/h8,24,26-43,45-48,55-68H,1,7,9-22H2,2-6H3,(H,69,70)/t24-,26-,27+,28+,29+,30+,31+,32+,33+,34+,35+,36-,37-,38-,39+,40+,41+,42-,43+,45-,46-,47-,48+,51-,52+,53+,54-/m0/s1
• InChI Key: QCSJRNNSTFHPAZ-SNDIJUFTSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₆O₂₅
• Molecular Weight: 1135.20 g/mol
• Exact Mass: 1134.54581822 g/mol
• Topological Polar Surface Area (TPSA): 411.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -2.80
• H-Bond Acceptor: 24
• H-Bond Donor: 15
• Rotatable Bonds: 17

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7412	74.12%
Caco-2	-	0.8770	87.70%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8514	85.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8272	82.72%
OATP1B3 inhibitior	-	0.4149	41.49%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5276	52.76%
BSEP inhibitior	+	0.8274	82.74%
P-glycoprotein inhibitior	+	0.7447	74.47%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7242	72.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8834	88.34%
CYP3A4 inhibition	-	0.7385	73.85%
CYP2C9 inhibition	-	0.8388	83.88%
CYP2C19 inhibition	-	0.8911	89.11%
CYP2D6 inhibition	-	0.9464	94.64%
CYP1A2 inhibition	-	0.8860	88.60%
CYP2C8 inhibition	+	0.7657	76.57%
CYP inhibitory promiscuity	-	0.9736	97.36%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6233	62.33%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9012	90.12%
Skin irritation	-	0.5687	56.87%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.8170	81.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7811	78.11%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.8425	84.25%
skin sensitisation	-	0.8870	88.70%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.5661	56.61%
Acute Oral Toxicity (c)	III	0.8004	80.04%
Estrogen receptor binding	+	0.8100	81.00%
Androgen receptor binding	+	0.7467	74.67%
Thyroid receptor binding	+	0.5132	51.32%
Glucocorticoid receptor binding	+	0.7228	72.28%
Aromatase binding	+	0.6235	62.35%
PPAR gamma	+	0.7932	79.32%
Honey bee toxicity	-	0.7215	72.15%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6705	67.05%
Fish aquatic toxicity	+	0.9787	97.87%

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	99.32%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.65%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.92%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	96.39%	95.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.05%	97.09%
CHEMBL2581	P07339	Cathepsin D	89.41%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.07%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	88.97%	92.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.16%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.68%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.57%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.02%	86.92%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.49%	96.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.75%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.27%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.85%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.41%	95.89%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.24%	83.57%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.33%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.14%	96.90%

Plants that contains it

• Dianthus japonicus
• Vaccaria hispanica

Cross-Links

• PubChem: 102317032
• NPASS: NPC75519
• LOTUS: LTS0104357
• wikiData: Q105218536