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(1R,2S,5S,6S,9R,12S,13S,16S,18R)-16-[(2R,3S,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-2-hydroxy-13-methylspiro[7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icosane-6,4'-oxolane]-2'-one

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 8cbb5415-1a59-4bda-935e-97b48a1f9ba3
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
IUPAC Name (1R,2S,5S,6S,9R,12S,13S,16S,18R)-16-[(2R,3S,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-2-hydroxy-13-methylspiro[7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icosane-6,4'-oxolane]-2'-one
SMILES (Canonical) CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC56C4(CCC5C7(CC(=O)OC7)OC6)O)C)O)OC)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@@]56[C@@]4(CC[C@@H]5[C@]7(CC(=O)OC7)OC6)O)C)O)OC)O
InChI InChI=1S/C30H46O9/c1-16-23(32)25(35-3)24(33)26(38-16)39-18-6-9-27(2)17(12-18)4-5-20-19(27)7-10-28-14-37-29(13-22(31)36-15-29)21(28)8-11-30(20,28)34/h16-21,23-26,32-34H,4-15H2,1-3H3/t16-,17+,18-,19-,20+,21-,23-,24-,25+,26-,27-,28-,29+,30-/m0/s1
InChI Key SAHFSRBBUCJJGW-PQYUPMBDSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C30H46O9
Molecular Weight 550.70 g/mol
Exact Mass 550.31418304 g/mol
Topological Polar Surface Area (TPSA) 124.00 Ų
XlogP 1.80
Atomic LogP (AlogP) 2.32
H-Bond Acceptor 9
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,2S,5S,6S,9R,12S,13S,16S,18R)-16-[(2R,3S,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-2-hydroxy-13-methylspiro[7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icosane-6,4'-oxolane]-2'-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8014 80.14%
Caco-2 - 0.8165 81.65%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.7000 70.00%
OATP2B1 inhibitior - 0.5798 57.98%
OATP1B1 inhibitior + 0.8697 86.97%
OATP1B3 inhibitior + 0.9430 94.30%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior - 0.5876 58.76%
P-glycoprotein inhibitior + 0.5731 57.31%
P-glycoprotein substrate + 0.6467 64.67%
CYP3A4 substrate + 0.7336 73.36%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8872 88.72%
CYP3A4 inhibition - 0.9292 92.92%
CYP2C9 inhibition - 0.9163 91.63%
CYP2C19 inhibition - 0.9073 90.73%
CYP2D6 inhibition - 0.9537 95.37%
CYP1A2 inhibition - 0.9216 92.16%
CYP2C8 inhibition - 0.5873 58.73%
CYP inhibitory promiscuity - 0.9694 96.94%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5833 58.33%
Eye corrosion - 0.9905 99.05%
Eye irritation - 0.9293 92.93%
Skin irritation - 0.6769 67.69%
Skin corrosion - 0.9404 94.04%
Ames mutagenesis - 0.6854 68.54%
Human Ether-a-go-go-Related Gene inhibition + 0.6743 67.43%
Micronuclear - 0.8800 88.00%
Hepatotoxicity - 0.7456 74.56%
skin sensitisation - 0.9290 92.90%
Respiratory toxicity + 0.8222 82.22%
Reproductive toxicity + 0.7778 77.78%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity + 0.5419 54.19%
Acute Oral Toxicity (c) I 0.6706 67.06%
Estrogen receptor binding + 0.7025 70.25%
Androgen receptor binding + 0.7263 72.63%
Thyroid receptor binding - 0.6065 60.65%
Glucocorticoid receptor binding + 0.6203 62.03%
Aromatase binding + 0.6753 67.53%
PPAR gamma + 0.5470 54.70%
Honey bee toxicity - 0.6139 61.39%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity + 0.6200 62.00%
Fish aquatic toxicity + 0.7697 76.97%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.30% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.19% 94.45%
CHEMBL204 P00734 Thrombin 95.76% 96.01%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.63% 96.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 94.17% 100.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 93.68% 96.77%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.07% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.82% 89.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 89.00% 92.94%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 88.99% 95.89%
CHEMBL1871 P10275 Androgen Receptor 88.88% 96.43%
CHEMBL253 P34972 Cannabinoid CB2 receptor 87.60% 97.25%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.36% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.14% 86.33%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 86.06% 82.69%
CHEMBL5255 O00206 Toll-like receptor 4 85.80% 92.50%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.24% 99.23%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 84.19% 93.04%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.13% 94.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.09% 95.56%
CHEMBL3714130 P46095 G-protein coupled receptor 6 83.70% 97.36%
CHEMBL2581 P07339 Cathepsin D 81.90% 98.95%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.65% 91.07%
CHEMBL1951 P21397 Monoamine oxidase A 80.42% 91.49%

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.
Cascabela thevetia
Stenostomum acreanum
Uncaria guianensis

Cross-Links

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PubChem 162981104
LOTUS LTS0221335
wikiData Q105226674