12-Deacetyl-12-epi-19-deoxyscalarin

Details

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Internal ID a9a8ab47-f5ce-4019-b69f-0841e3bef577
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids > Scalarane sesterterpenoids
IUPAC Name (5aS,5bR,7aS,11aS,11bR,13R,13aS,13bR)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[2,1-e][2]benzofuran-3-one
SMILES (Canonical) CC1(CCCC2(C1CCC3(C2CC(C4(C3CC=C5C4COC5=O)C)O)C)C)C
SMILES (Isomeric) C[C@]12CCCC([C@@H]1CC[C@@]3([C@@H]2C[C@H]([C@]4([C@H]3CC=C5[C@@H]4COC5=O)C)O)C)(C)C
InChI InChI=1S/C25H38O3/c1-22(2)10-6-11-23(3)17(22)9-12-24(4)18-8-7-15-16(14-28-21(15)27)25(18,5)20(26)13-19(23)24/h7,16-20,26H,6,8-14H2,1-5H3/t16-,17-,18-,19+,20+,23-,24-,25+/m0/s1
InChI Key XJAQPGLKAWWKLX-JBPGZYRBSA-N
Popularity 10 references in papers

Physical and Chemical Properties

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Molecular Formula C25H38O3
Molecular Weight 386.60 g/mol
Exact Mass 386.28209507 g/mol
Topological Polar Surface Area (TPSA) 46.50 Ų
XlogP 6.20
Atomic LogP (AlogP) 5.13
H-Bond Acceptor 3
H-Bond Donor 1
Rotatable Bonds 0

Synonyms

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12-deacetyl-12-epi-19-deoxyscalarin
25-dehydroxy-12-epi-deacetylscalarin
12-epi-O-deacetyl-19-deoxyscalarin
BDBM50226463
12-O-deacetyl-12-epi-19-deoxyscalarin
12-O-deacetyl-25-deoxy-12-episcalarin
(5aS,5bR,7aS,11aS,11bR,13R,13aS,13bR)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-1,5,5a,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-hexadecahydrochryseno[2,1-c]furan-3(5bH)-one

2D Structure

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2D Structure of 12-Deacetyl-12-epi-19-deoxyscalarin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9960 99.60%
Caco-2 + 0.5992 59.92%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.8196 81.96%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8910 89.10%
OATP1B3 inhibitior + 0.9841 98.41%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior + 0.6750 67.50%
BSEP inhibitior + 0.9386 93.86%
P-glycoprotein inhibitior - 0.6610 66.10%
P-glycoprotein substrate - 0.7707 77.07%
CYP3A4 substrate + 0.6563 65.63%
CYP2C9 substrate - 0.7907 79.07%
CYP2D6 substrate - 0.8724 87.24%
CYP3A4 inhibition - 0.7545 75.45%
CYP2C9 inhibition - 0.8436 84.36%
CYP2C19 inhibition - 0.8021 80.21%
CYP2D6 inhibition - 0.9036 90.36%
CYP1A2 inhibition - 0.7568 75.68%
CYP2C8 inhibition - 0.7140 71.40%
CYP inhibitory promiscuity - 0.8717 87.17%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5186 51.86%
Eye corrosion - 0.9913 99.13%
Eye irritation - 0.9231 92.31%
Skin irritation + 0.5575 55.75%
Skin corrosion - 0.9387 93.87%
Ames mutagenesis - 0.7900 79.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6558 65.58%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.5875 58.75%
skin sensitisation - 0.7471 74.71%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity - 0.6144 61.44%
Acute Oral Toxicity (c) III 0.7320 73.20%
Estrogen receptor binding + 0.8100 81.00%
Androgen receptor binding + 0.6590 65.90%
Thyroid receptor binding + 0.6962 69.62%
Glucocorticoid receptor binding + 0.8458 84.58%
Aromatase binding + 0.7281 72.81%
PPAR gamma + 0.6657 66.57%
Honey bee toxicity - 0.8435 84.35%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9897 98.97%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL2047 Q96RI1 Bile acid receptor FXR 31600 nM
IC50
PMID: 17988093

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL4040 P28482 MAP kinase ERK2 99.68% 83.82%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.05% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.88% 97.25%
CHEMBL2581 P07339 Cathepsin D 93.67% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.51% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.16% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.18% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 89.28% 82.69%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.42% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.86% 99.23%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.23% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.20% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.03% 94.45%
CHEMBL1937 Q92769 Histone deacetylase 2 81.33% 94.75%

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.
Albizia adinocephala
Pimpinella aurea

Cross-Links

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PubChem 10572244
NPASS NPC110496
ChEMBL CHEMBL250263
LOTUS LTS0007697
wikiData Q104911019