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(3S,5S,8R,9S,10S,12R,13S,14S,17R)-5,12,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5S,6R)-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]phenanthrene-10-carboxylic acid

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 1f18cc6a-9f63-4e8d-8288-173b51a6578f
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
IUPAC Name (3S,5S,8R,9S,10S,12R,13S,14S,17R)-5,12,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5S,6R)-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]phenanthrene-10-carboxylic acid
SMILES (Canonical) CC1C(C(C(C(O1)OC2CCC3(C4CC(C5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)O)C(=O)O)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]4C[C@H]([C@@]5([C@H](CC[C@@]5([C@@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)O)C(=O)O)O)O)O
InChI InChI=1S/C29H42O12/c1-13-21(32)22(33)23(34)24(40-13)41-15-3-7-28(25(35)36)18-10-19(30)26(2)16(14-9-20(31)39-12-14)5-8-29(26,38)17(18)4-6-27(28,37)11-15/h9,13,15-19,21-24,30,32-34,37-38H,3-8,10-12H2,1-2H3,(H,35,36)/t13-,15+,16-,17-,18+,19-,21-,22-,23-,24+,26+,27+,28-,29+/m1/s1
InChI Key PQWNIWYZNGKIOH-GCEASFGNSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C29H42O12
Molecular Weight 582.60 g/mol
Exact Mass 582.26762677 g/mol
Topological Polar Surface Area (TPSA) 203.00 Ų
XlogP -1.80
Atomic LogP (AlogP) -0.39
H-Bond Acceptor 11
H-Bond Donor 7
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3S,5S,8R,9S,10S,12R,13S,14S,17R)-5,12,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5S,6R)-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]phenanthrene-10-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8810 88.10%
Caco-2 - 0.8730 87.30%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.8768 87.68%
OATP2B1 inhibitior - 0.7459 74.59%
OATP1B1 inhibitior + 0.9260 92.60%
OATP1B3 inhibitior + 0.9707 97.07%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.8314 83.14%
P-glycoprotein inhibitior - 0.4859 48.59%
P-glycoprotein substrate + 0.6750 67.50%
CYP3A4 substrate + 0.6860 68.60%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9027 90.27%
CYP3A4 inhibition - 0.9374 93.74%
CYP2C9 inhibition - 0.9172 91.72%
CYP2C19 inhibition - 0.9401 94.01%
CYP2D6 inhibition - 0.9265 92.65%
CYP1A2 inhibition - 0.9285 92.85%
CYP2C8 inhibition - 0.6477 64.77%
CYP inhibitory promiscuity - 0.9477 94.77%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5778 57.78%
Eye corrosion - 0.9886 98.86%
Eye irritation - 0.9334 93.34%
Skin irritation - 0.5669 56.69%
Skin corrosion - 0.9242 92.42%
Ames mutagenesis - 0.6424 64.24%
Human Ether-a-go-go-Related Gene inhibition + 0.8663 86.63%
Micronuclear - 0.7000 70.00%
Hepatotoxicity - 0.7125 71.25%
skin sensitisation - 0.8922 89.22%
Respiratory toxicity + 0.8556 85.56%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity - 0.8196 81.96%
Acute Oral Toxicity (c) I 0.7842 78.42%
Estrogen receptor binding + 0.8610 86.10%
Androgen receptor binding + 0.7984 79.84%
Thyroid receptor binding - 0.6082 60.82%
Glucocorticoid receptor binding + 0.6559 65.59%
Aromatase binding + 0.7240 72.40%
PPAR gamma + 0.5452 54.52%
Honey bee toxicity - 0.7725 77.25%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9651 96.51%

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 97.97% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.91% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.66% 86.33%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.19% 85.14%
CHEMBL3714130 P46095 G-protein coupled receptor 6 93.46% 97.36%
CHEMBL1994 P08235 Mineralocorticoid receptor 93.34% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.21% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.24% 89.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 88.59% 97.25%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.09% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.00% 95.56%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 86.17% 81.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.15% 94.45%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 83.16% 93.04%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 82.19% 96.77%
CHEMBL4208 P20618 Proteasome component C5 81.28% 90.00%
CHEMBL5255 O00206 Toll-like receptor 4 80.82% 92.50%

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.
Antiaris toxicaria

Cross-Links

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PubChem 73350760
LOTUS LTS0018288
wikiData Q105213504