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(1S,2S,4R,6S,11R,12S,14R,16S,17R,18S,21S)-14,18-dihydroxy-16-[(2R)-2-hydroxy-3,4-dimethyl-5-oxofuran-2-yl]-11,17,21-trimethyl-5,15-dioxahexacyclo[12.6.1.02,12.04,6.06,11.018,21]henicos-8-en-10-one

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 87d99d6a-1aab-4854-9858-6d173a0dedeb
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1S,2S,4R,6S,11R,12S,14R,16S,17R,18S,21S)-14,18-dihydroxy-16-[(2R)-2-hydroxy-3,4-dimethyl-5-oxofuran-2-yl]-11,17,21-trimethyl-5,15-dioxahexacyclo[12.6.1.02,12.04,6.06,11.018,21]henicos-8-en-10-one
SMILES (Canonical) CC1C(OC2(CC3C(CC4C5(C3(C(=O)C=CC5)C)O4)C6C2(C1(CC6)O)C)O)C7(C(=C(C(=O)O7)C)C)O
SMILES (Isomeric) C[C@@H]1[C@H](O[C@@]2(C[C@H]3[C@@H](C[C@@H]4[C@]5([C@@]3(C(=O)C=CC5)C)O4)[C@H]6[C@]2([C@@]1(CC6)O)C)O)[C@]7(C(=C(C(=O)O7)C)C)O
InChI InChI=1S/C28H36O8/c1-13-14(2)28(33,36-22(13)30)21-15(3)25(31)10-8-17-16-11-20-26(34-20)9-6-7-19(29)23(26,4)18(16)12-27(32,35-21)24(17,25)5/h6-7,15-18,20-21,31-33H,8-12H2,1-5H3/t15-,16+,17+,18+,20-,21+,23+,24+,25+,26-,27-,28-/m1/s1
InChI Key BKIOKGBFWGEDDM-XYALGXENSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H36O8
Molecular Weight 500.60 g/mol
Exact Mass 500.24101810 g/mol
Topological Polar Surface Area (TPSA) 126.00 Ų
XlogP 1.20
Atomic LogP (AlogP) 2.15
H-Bond Acceptor 8
H-Bond Donor 3
Rotatable Bonds 1

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,2S,4R,6S,11R,12S,14R,16S,17R,18S,21S)-14,18-dihydroxy-16-[(2R)-2-hydroxy-3,4-dimethyl-5-oxofuran-2-yl]-11,17,21-trimethyl-5,15-dioxahexacyclo[12.6.1.02,12.04,6.06,11.018,21]henicos-8-en-10-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9434 94.34%
Caco-2 - 0.6781 67.81%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.6969 69.69%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8718 87.18%
OATP1B3 inhibitior + 0.9625 96.25%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8821 88.21%
BSEP inhibitior + 0.9468 94.68%
P-glycoprotein inhibitior - 0.4823 48.23%
P-glycoprotein substrate + 0.6618 66.18%
CYP3A4 substrate + 0.7221 72.21%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8828 88.28%
CYP3A4 inhibition - 0.7105 71.05%
CYP2C9 inhibition - 0.8527 85.27%
CYP2C19 inhibition - 0.8871 88.71%
CYP2D6 inhibition - 0.9406 94.06%
CYP1A2 inhibition - 0.8662 86.62%
CYP2C8 inhibition + 0.5958 59.58%
CYP inhibitory promiscuity - 0.9464 94.64%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5016 50.16%
Eye corrosion - 0.9878 98.78%
Eye irritation - 0.9288 92.88%
Skin irritation - 0.5508 55.08%
Skin corrosion - 0.8987 89.87%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7213 72.13%
Micronuclear - 0.6300 63.00%
Hepatotoxicity - 0.5309 53.09%
skin sensitisation - 0.8321 83.21%
Respiratory toxicity + 0.8778 87.78%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8625 86.25%
Nephrotoxicity - 0.6184 61.84%
Acute Oral Toxicity (c) I 0.5473 54.73%
Estrogen receptor binding + 0.8643 86.43%
Androgen receptor binding + 0.7692 76.92%
Thyroid receptor binding + 0.6221 62.21%
Glucocorticoid receptor binding + 0.7900 79.00%
Aromatase binding + 0.8077 80.77%
PPAR gamma + 0.6171 61.71%
Honey bee toxicity - 0.7802 78.02%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.9641 96.41%

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 95.88% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.11% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.49% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.58% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.12% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.69% 99.23%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.14% 100.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 88.38% 97.14%
CHEMBL2581 P07339 Cathepsin D 87.39% 98.95%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 86.96% 97.33%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.24% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.01% 89.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 83.56% 93.04%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 83.40% 93.03%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.14% 97.25%
CHEMBL1937 Q92769 Histone deacetylase 2 82.01% 94.75%
CHEMBL4208 P20618 Proteasome component C5 81.83% 90.00%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 81.16% 86.00%
CHEMBL259 P32245 Melanocortin receptor 4 80.47% 95.38%

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 caulescens

Cross-Links

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PubChem 162902950
LOTUS LTS0041779
wikiData Q104937615