4,5,13,17-tetrahydroxy-4',5',10,16,20-pentamethylspiro[14-oxapentacyclo[11.6.1.02,11.05,10.017,20]icos-7-ene-15,2'-3H-pyran]-6',9-dione

Details

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Internal ID cfa86cdb-35b3-4758-970d-f18976286caa
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name 4,5,13,17-tetrahydroxy-4',5',10,16,20-pentamethylspiro[14-oxapentacyclo[11.6.1.02,11.05,10.017,20]icos-7-ene-15,2'-3H-pyran]-6',9-dione
SMILES (Canonical) CC1C2(CCC3C2(C(CC4C3CC(C5(C4(C(=O)C=CC5)C)O)O)(OC16CC(=C(C(=O)O6)C)C)O)C)O
SMILES (Isomeric) CC1C2(CCC3C2(C(CC4C3CC(C5(C4(C(=O)C=CC5)C)O)O)(OC16CC(=C(C(=O)O6)C)C)O)C)O
InChI InChI=1S/C28H38O8/c1-14-12-27(35-22(31)15(14)2)16(3)25(32)10-8-18-17-11-21(30)26(33)9-6-7-20(29)23(26,4)19(17)13-28(34,36-27)24(18,25)5/h6-7,16-19,21,30,32-34H,8-13H2,1-5H3
InChI Key PMNDUEXLEMOCBZ-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H38O8
Molecular Weight 502.60 g/mol
Exact Mass 502.25666817 g/mol
Topological Polar Surface Area (TPSA) 134.00 Ų
XlogP 1.30
Atomic LogP (AlogP) 2.14
H-Bond Acceptor 8
H-Bond Donor 4
Rotatable Bonds 0

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 4,5,13,17-tetrahydroxy-4',5',10,16,20-pentamethylspiro[14-oxapentacyclo[11.6.1.02,11.05,10.017,20]icos-7-ene-15,2'-3H-pyran]-6',9-dione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8628 86.28%
Caco-2 - 0.6846 68.46%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.7058 70.58%
OATP2B1 inhibitior - 0.8642 86.42%
OATP1B1 inhibitior + 0.8626 86.26%
OATP1B3 inhibitior + 0.8839 88.39%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.6124 61.24%
BSEP inhibitior + 0.9456 94.56%
P-glycoprotein inhibitior - 0.5000 50.00%
P-glycoprotein substrate + 0.5767 57.67%
CYP3A4 substrate + 0.7170 71.70%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8798 87.98%
CYP3A4 inhibition - 0.8648 86.48%
CYP2C9 inhibition - 0.9390 93.90%
CYP2C19 inhibition - 0.9333 93.33%
CYP2D6 inhibition - 0.9618 96.18%
CYP1A2 inhibition - 0.9057 90.57%
CYP2C8 inhibition + 0.5780 57.80%
CYP inhibitory promiscuity - 0.9834 98.34%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5529 55.29%
Eye corrosion - 0.9924 99.24%
Eye irritation - 0.9386 93.86%
Skin irritation + 0.6519 65.19%
Skin corrosion - 0.9034 90.34%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4311 43.11%
Micronuclear - 0.8000 80.00%
Hepatotoxicity - 0.5125 51.25%
skin sensitisation - 0.8425 84.25%
Respiratory toxicity + 0.8556 85.56%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8625 86.25%
Nephrotoxicity + 0.4688 46.88%
Acute Oral Toxicity (c) I 0.4669 46.69%
Estrogen receptor binding + 0.8052 80.52%
Androgen receptor binding + 0.7815 78.15%
Thyroid receptor binding + 0.6033 60.33%
Glucocorticoid receptor binding + 0.7919 79.19%
Aromatase binding + 0.7885 78.85%
PPAR gamma + 0.6464 64.64%
Honey bee toxicity - 0.7983 79.83%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9729 97.29%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.24% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.90% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.41% 95.56%
CHEMBL2581 P07339 Cathepsin D 93.33% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 92.56% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.11% 96.09%
CHEMBL1937 Q92769 Histone deacetylase 2 91.28% 94.75%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.25% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.23% 97.09%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 90.22% 86.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.66% 99.23%
CHEMBL1871 P10275 Androgen Receptor 88.16% 96.43%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.94% 97.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.95% 86.33%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.11% 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.
Jaborosa rotacea

Cross-Links

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PubChem 73017083
LOTUS LTS0128077
wikiData Q105211609