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Sarmentoloside

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 28ec94f7-135d-40ae-b29c-d18e6a363f35
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
IUPAC Name 3-[(3S,5S,8R,9S,10R,11R,13R,14S,17R)-5,11,14-trihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
SMILES (Canonical) CC1C(C(C(C(O1)OC2CCC3(C4C(CCC3(C2)O)C5(CCC(C5(CC4O)C)C6=CC(=O)OC6)O)CO)O)O)O
SMILES (Isomeric) C[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@@H]4[C@@H](CC[C@@]3(C2)O)[C@]5(CC[C@@H]([C@]5(C[C@H]4O)C)C6=CC(=O)OC6)O)CO)O)O)O
InChI InChI=1S/C29H44O11/c1-14-22(33)23(34)24(35)25(39-14)40-16-3-6-27(13-30)21-18(4-7-28(27,36)10-16)29(37)8-5-17(15-9-20(32)38-12-15)26(29,2)11-19(21)31/h9,14,16-19,21-25,30-31,33-37H,3-8,10-13H2,1-2H3/t14-,16-,17+,18+,19+,21+,22+,23+,24+,25-,26+,27-,28-,29-/m0/s1
InChI Key BUGNRCRUPAIYMD-VBVNMADNSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H44O11
Molecular Weight 568.70 g/mol
Exact Mass 568.28836222 g/mol
Topological Polar Surface Area (TPSA) 186.00 Ų
XlogP -1.80
Atomic LogP (AlogP) -0.49
H-Bond Acceptor 11
H-Bond Donor 7
Rotatable Bonds 4

Synonyms

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6847-59-2
C08878
Sarmentologenin 3-O-(6-deoxy-alpha-L-taloside)
3-[(3S,5S,8R,9S,10R,11R,13R,14S,17R)-5,11,14-trihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
AC1L9BTB
CHEBI:9032
DTXSID20331646
Q27108223
3-[(3S,5S,8R,9S,10R,11R,13R,14S,17R)-5,11,14-trihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

2D Structure

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2D Structure of Sarmentoloside

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8248 82.48%
Caco-2 - 0.8694 86.94%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.8382 83.82%
OATP2B1 inhibitior - 0.6757 67.57%
OATP1B1 inhibitior + 0.9316 93.16%
OATP1B3 inhibitior + 0.9481 94.81%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.8479 84.79%
P-glycoprotein inhibitior - 0.5190 51.90%
P-glycoprotein substrate - 0.5984 59.84%
CYP3A4 substrate + 0.7058 70.58%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9010 90.10%
CYP3A4 inhibition - 0.9241 92.41%
CYP2C9 inhibition - 0.9242 92.42%
CYP2C19 inhibition - 0.9271 92.71%
CYP2D6 inhibition - 0.9231 92.31%
CYP1A2 inhibition - 0.9045 90.45%
CYP2C8 inhibition + 0.4583 45.83%
CYP inhibitory promiscuity - 0.9179 91.79%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6086 60.86%
Eye corrosion - 0.9907 99.07%
Eye irritation - 0.9388 93.88%
Skin irritation - 0.5648 56.48%
Skin corrosion - 0.9423 94.23%
Ames mutagenesis - 0.6770 67.70%
Human Ether-a-go-go-Related Gene inhibition + 0.8699 86.99%
Micronuclear - 0.8600 86.00%
Hepatotoxicity - 0.6677 66.77%
skin sensitisation - 0.9189 91.89%
Respiratory toxicity + 0.8333 83.33%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity - 0.7965 79.65%
Acute Oral Toxicity (c) I 0.8357 83.57%
Estrogen receptor binding + 0.8587 85.87%
Androgen receptor binding + 0.8274 82.74%
Thyroid receptor binding - 0.6006 60.06%
Glucocorticoid receptor binding + 0.5695 56.95%
Aromatase binding + 0.7041 70.41%
PPAR gamma + 0.5454 54.54%
Honey bee toxicity - 0.7645 76.45%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9498 94.98%

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 98.56% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.70% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.68% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.81% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 95.73% 100.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.65% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.49% 97.09%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 94.35% 96.77%
CHEMBL2581 P07339 Cathepsin D 93.21% 98.95%
CHEMBL3714130 P46095 G-protein coupled receptor 6 91.86% 97.36%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.17% 94.45%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.40% 95.89%
CHEMBL226 P30542 Adenosine A1 receptor 88.41% 95.93%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.97% 89.00%
CHEMBL1937 Q92769 Histone deacetylase 2 85.30% 94.75%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.08% 95.56%
CHEMBL3038469 P24941 CDK2/Cyclin A 85.05% 91.38%
CHEMBL241 Q14432 Phosphodiesterase 3A 83.57% 92.94%
CHEMBL4208 P20618 Proteasome component C5 83.05% 90.00%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 82.82% 81.11%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.39% 94.00%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 81.22% 96.21%
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 80.83% 83.57%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.06% 93.04%

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.
Asarum sieboldii
Strophanthus divaricatus

Cross-Links

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PubChem 441869
NPASS NPC311516
LOTUS LTS0113430
wikiData Q27108223