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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-carbaldehyde

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 94286bea-0089-49f3-9352-236615bd85d0
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-carbaldehyde
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
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
InChI InChI=1S/C29H42O11/c1-14-22(33)23(34)24(35)25(39-14)40-16-3-6-27(13-30)19-10-20(31)26(2)17(15-9-21(32)38-12-15)5-8-29(26,37)18(19)4-7-28(27,36)11-16/h9,13-14,16-20,22-25,31,33-37H,3-8,10-12H2,1-2H3/t14-,16+,17-,18-,19+,20-,22-,23-,24-,25+,26+,27+,28+,29+/m1/s1
InChI Key MFIXZHBJWSBQJA-YFENXAIXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C29H42O11
Molecular Weight 566.60 g/mol
Exact Mass 566.27271215 g/mol
Topological Polar Surface Area (TPSA) 183.00 Ų
XlogP -1.80
Atomic LogP (AlogP) -0.28
H-Bond Acceptor 11
H-Bond Donor 6
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-carbaldehyde

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 - 0.8654 86.54%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.8768 87.68%
OATP2B1 inhibitior - 0.7445 74.45%
OATP1B1 inhibitior + 0.9341 93.41%
OATP1B3 inhibitior + 0.9707 97.07%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.6051 60.51%
P-glycoprotein inhibitior - 0.4693 46.93%
P-glycoprotein substrate + 0.7098 70.98%
CYP3A4 substrate + 0.6836 68.36%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8978 89.78%
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 - 0.6619 66.19%
CYP inhibitory promiscuity - 0.9477 94.77%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5778 57.78%
Eye corrosion - 0.9886 98.86%
Eye irritation - 0.9390 93.90%
Skin irritation - 0.5669 56.69%
Skin corrosion - 0.9242 92.42%
Ames mutagenesis - 0.5170 51.70%
Human Ether-a-go-go-Related Gene inhibition + 0.8855 88.55%
Micronuclear - 0.7000 70.00%
Hepatotoxicity - 0.7176 71.76%
skin sensitisation - 0.8922 89.22%
Respiratory toxicity + 0.8778 87.78%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity - 0.7933 79.33%
Acute Oral Toxicity (c) I 0.7842 78.42%
Estrogen receptor binding + 0.8500 85.00%
Androgen receptor binding + 0.8084 80.84%
Thyroid receptor binding - 0.5777 57.77%
Glucocorticoid receptor binding + 0.6566 65.66%
Aromatase binding + 0.7136 71.36%
PPAR gamma + 0.5569 55.69%
Honey bee toxicity - 0.7368 73.68%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity + 0.5500 55.00%
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 98.61% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.59% 96.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 94.72% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.60% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.93% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.87% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.41% 97.25%
CHEMBL3714130 P46095 G-protein coupled receptor 6 92.30% 97.36%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.30% 89.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.29% 85.14%
CHEMBL226 P30542 Adenosine A1 receptor 88.05% 95.93%
CHEMBL4208 P20618 Proteasome component C5 86.74% 90.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.58% 94.45%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 84.29% 82.69%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.43% 99.23%
CHEMBL2581 P07339 Cathepsin D 82.53% 98.95%
CHEMBL3492 P49721 Proteasome Macropain subunit 81.57% 90.24%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 81.47% 96.00%
CHEMBL1937 Q92769 Histone deacetylase 2 80.99% 94.75%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 80.57% 96.77%
CHEMBL1871 P10275 Androgen Receptor 80.28% 96.43%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 80.19% 86.00%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 80.08% 93.40%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 80.01% 94.80%
CHEMBL4829 O00763 Acetyl-CoA carboxylase 2 80.00% 98.00%

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 73349184
LOTUS LTS0270760
wikiData Q105162761