(2S,3R,8S,9S,10R,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-2,3,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-7,11-dione

Details

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Internal ID 90fb261d-5722-4f75-9d9e-be64254761d8
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
IUPAC Name (2S,3R,8S,9S,10R,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-2,3,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-7,11-dione
SMILES (Canonical) CC1(C(C(CC2C1=CC(=O)C3C2(C(=O)CC4(C3(CC(C4C(C)(C(=O)CCC(C)(C)O)O)O)C)C)C)O)O)C
SMILES (Isomeric) C[C@@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]3([C@H]2C(=O)C=C4[C@H]3C[C@@H]([C@@H](C4(C)C)O)O)C)C)[C@](C)(C(=O)CCC(C)(C)O)O)O
InChI InChI=1S/C30H46O8/c1-25(2,37)10-9-20(34)30(8,38)23-19(33)13-27(5)22-17(31)11-15-16(12-18(32)24(36)26(15,3)4)29(22,7)21(35)14-28(23,27)6/h11,16,18-19,22-24,32-33,36-38H,9-10,12-14H2,1-8H3/t16-,18+,19-,22+,23+,24+,27+,28-,29-,30+/m1/s1
InChI Key CEXXNUWIPXZZMB-CASDGZEASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C30H46O8
Molecular Weight 534.70 g/mol
Exact Mass 534.31926842 g/mol
Topological Polar Surface Area (TPSA) 152.00 Ų
XlogP 0.90
Atomic LogP (AlogP) 2.12
H-Bond Acceptor 8
H-Bond Donor 5
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3R,8S,9S,10R,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-2,3,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-7,11-dione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9834 98.34%
Caco-2 - 0.6543 65.43%
Blood Brain Barrier + 0.8388 83.88%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.8055 80.55%
OATP2B1 inhibitior - 0.8607 86.07%
OATP1B1 inhibitior + 0.8058 80.58%
OATP1B3 inhibitior + 0.8748 87.48%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.7532 75.32%
BSEP inhibitior + 0.6135 61.35%
P-glycoprotein inhibitior - 0.4701 47.01%
P-glycoprotein substrate + 0.5205 52.05%
CYP3A4 substrate + 0.6721 67.21%
CYP2C9 substrate - 0.8086 80.86%
CYP2D6 substrate - 0.8838 88.38%
CYP3A4 inhibition - 0.8060 80.60%
CYP2C9 inhibition - 0.8389 83.89%
CYP2C19 inhibition - 0.7834 78.34%
CYP2D6 inhibition - 0.9541 95.41%
CYP1A2 inhibition - 0.9254 92.54%
CYP2C8 inhibition - 0.6020 60.20%
CYP inhibitory promiscuity - 0.9150 91.50%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6943 69.43%
Eye corrosion - 0.9929 99.29%
Eye irritation - 0.9146 91.46%
Skin irritation + 0.6254 62.54%
Skin corrosion - 0.9371 93.71%
Ames mutagenesis - 0.6954 69.54%
Human Ether-a-go-go-Related Gene inhibition + 0.7332 73.32%
Micronuclear - 0.8500 85.00%
Hepatotoxicity - 0.5914 59.14%
skin sensitisation - 0.8018 80.18%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.9889 98.89%
Mitochondrial toxicity + 0.9500 95.00%
Nephrotoxicity - 0.7338 73.38%
Acute Oral Toxicity (c) I 0.5554 55.54%
Estrogen receptor binding + 0.7294 72.94%
Androgen receptor binding + 0.7609 76.09%
Thyroid receptor binding + 0.6436 64.36%
Glucocorticoid receptor binding + 0.7653 76.53%
Aromatase binding + 0.7245 72.45%
PPAR gamma + 0.5347 53.47%
Honey bee toxicity - 0.7543 75.43%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9933 99.33%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.66% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.38% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.71% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.33% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.58% 97.09%
CHEMBL2581 P07339 Cathepsin D 92.61% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.02% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.53% 95.56%
CHEMBL3746 P80365 11-beta-hydroxysteroid dehydrogenase 2 87.50% 94.78%
CHEMBL2996 Q05655 Protein kinase C delta 84.72% 97.79%
CHEMBL4208 P20618 Proteasome component C5 84.59% 90.00%
CHEMBL226 P30542 Adenosine A1 receptor 84.44% 95.93%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.36% 91.07%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.62% 86.33%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 82.41% 96.95%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.47% 99.23%

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.
Cayaponia racemosa

Cross-Links

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PubChem 163017432
LOTUS LTS0145459
wikiData Q104956192