(8R,9S,10R,12R,13S,14S,16S,17R)-12,16-dihydroxy-17-[(2S,3S,6R)-3-hydroxy-6-methyl-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

Details

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Internal ID 4b6ec869-8159-45af-89bd-e86fddd5b9cf
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
IUPAC Name (8R,9S,10R,12R,13S,14S,16S,17R)-12,16-dihydroxy-17-[(2S,3S,6R)-3-hydroxy-6-methyl-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
SMILES (Canonical) CC(CCC(C(C)C1C(CC2C1(C(CC3C2CCC4=CC(=O)CCC34C)O)C)O)O)COC5C(C(C(C(O5)CO)O)O)O
SMILES (Isomeric) C[C@H](CC[C@@H]([C@@H](C)[C@H]1[C@H](C[C@@H]2[C@@]1([C@@H](C[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)O)C)O)O)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
InChI InChI=1S/C33H54O10/c1-16(15-42-31-30(41)29(40)28(39)25(14-34)43-31)5-8-23(36)17(2)27-24(37)12-22-20-7-6-18-11-19(35)9-10-32(18,3)21(20)13-26(38)33(22,27)4/h11,16-17,20-31,34,36-41H,5-10,12-15H2,1-4H3/t16-,17-,20-,21+,22+,23+,24+,25-,26-,27+,28-,29+,30-,31-,32+,33-/m1/s1
InChI Key KBOYYAOBNDMUQQ-GILNANDQSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C33H54O10
Molecular Weight 610.80 g/mol
Exact Mass 610.37169792 g/mol
Topological Polar Surface Area (TPSA) 177.00 Ų
XlogP 1.50
Atomic LogP (AlogP) 1.31
H-Bond Acceptor 10
H-Bond Donor 7
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (8R,9S,10R,12R,13S,14S,16S,17R)-12,16-dihydroxy-17-[(2S,3S,6R)-3-hydroxy-6-methyl-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8236 82.36%
Caco-2 - 0.8646 86.46%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.7998 79.98%
OATP2B1 inhibitior - 0.5768 57.68%
OATP1B1 inhibitior + 0.8581 85.81%
OATP1B3 inhibitior + 0.8009 80.09%
MATE1 inhibitior - 0.9812 98.12%
OCT2 inhibitior - 0.7026 70.26%
BSEP inhibitior + 0.7246 72.46%
P-glycoprotein inhibitior + 0.6601 66.01%
P-glycoprotein substrate - 0.5076 50.76%
CYP3A4 substrate + 0.7271 72.71%
CYP2C9 substrate - 0.7956 79.56%
CYP2D6 substrate - 0.8844 88.44%
CYP3A4 inhibition - 0.9252 92.52%
CYP2C9 inhibition - 0.9146 91.46%
CYP2C19 inhibition - 0.9086 90.86%
CYP2D6 inhibition - 0.9402 94.02%
CYP1A2 inhibition - 0.8705 87.05%
CYP2C8 inhibition + 0.4939 49.39%
CYP inhibitory promiscuity - 0.9441 94.41%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6845 68.45%
Eye corrosion - 0.9912 99.12%
Eye irritation - 0.9404 94.04%
Skin irritation + 0.5131 51.31%
Skin corrosion - 0.9466 94.66%
Ames mutagenesis - 0.8351 83.51%
Human Ether-a-go-go-Related Gene inhibition - 0.3982 39.82%
Micronuclear - 0.8500 85.00%
Hepatotoxicity - 0.6351 63.51%
skin sensitisation - 0.9262 92.62%
Respiratory toxicity + 0.8667 86.67%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity - 0.9026 90.26%
Acute Oral Toxicity (c) III 0.5238 52.38%
Estrogen receptor binding + 0.6573 65.73%
Androgen receptor binding + 0.7975 79.75%
Thyroid receptor binding - 0.6315 63.15%
Glucocorticoid receptor binding + 0.6060 60.60%
Aromatase binding + 0.6452 64.52%
PPAR gamma + 0.5754 57.54%
Honey bee toxicity - 0.7178 71.78%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity - 0.7300 73.00%
Fish aquatic toxicity + 0.9397 93.97%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.46% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.51% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.48% 91.11%
CHEMBL226 P30542 Adenosine A1 receptor 97.07% 95.93%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.82% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 95.67% 100.00%
CHEMBL2581 P07339 Cathepsin D 94.09% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.57% 97.25%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.91% 89.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 88.69% 95.89%
CHEMBL1871 P10275 Androgen Receptor 86.88% 96.43%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.77% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.15% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.35% 95.56%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 81.59% 96.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.56% 95.89%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 80.52% 97.33%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.22% 92.62%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Crotalaria pallida
Dahlia pinnata
Gentiana manshurica
Hosta longipes
Rosa villosa

Cross-Links

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PubChem 71568834
NPASS NPC260665
ChEMBL CHEMBL2337721
LOTUS LTS0111963
wikiData Q104908844