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[(5aS,5bR,7aS,11aS,11bR,13R,13aS,13bR)-5b,8,8,11a,13a-pentamethyl-3-oxo-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[2,1-e]isobenzofuran-13-yl] acetate

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 1ec3dd15-5a31-4cf1-9d9e-81efb2592691
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids > Scalarane sesterterpenoids
IUPAC Name [(5aS,5bR,7aS,11aS,11bR,13R,13aS,13bR)-5b,8,8,11a,13a-pentamethyl-3-oxo-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[2,1-e][2]benzofuran-13-yl] acetate
SMILES (Canonical) CC(=O)OC1CC2C3(CCCC(C3CCC2(C4C1(C5COC(=O)C5=CC4)C)C)(C)C)C
SMILES (Isomeric) CC(=O)O[C@@H]1C[C@@H]2[C@]3(CCCC([C@@H]3CC[C@]2([C@H]4[C@]1([C@H]5COC(=O)C5=CC4)C)C)(C)C)C
InChI InChI=1S/C27H40O4/c1-16(28)31-22-14-21-25(4)12-7-11-24(2,3)19(25)10-13-26(21,5)20-9-8-17-18(27(20,22)6)15-30-23(17)29/h8,18-22H,7,9-15H2,1-6H3/t18-,19-,20-,21+,22+,25-,26-,27+/m0/s1
InChI Key BTGJLMDMCKFWNM-MGHNXQGFSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C27H40O4
Molecular Weight 428.60 g/mol
Exact Mass 428.29265975 g/mol
Topological Polar Surface Area (TPSA) 52.60 Ų
XlogP 6.80
Atomic LogP (AlogP) 5.70
H-Bond Acceptor 4
H-Bond Donor 0
Rotatable Bonds 1

Synonyms

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[(5aS,5bR,7aS,11aS,11bR,13R,13aS,13bR)-5b,8,8,11a,13a-pentamethyl-3-oxo-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[2,1-e]isobenzofuran-13-yl] acetate
Chryseno[1,2-c]furan-3(1H)-one, 13-(acetyloxy)-5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-hexadecahydro-5b,8,8,11a,13a-pentamethyl-, (5aS,5bR,7aS,11aS,11bR,13R,13aS,13bR)-

2D Structure

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2D Structure of [(5aS,5bR,7aS,11aS,11bR,13R,13aS,13bR)-5b,8,8,11a,13a-pentamethyl-3-oxo-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[2,1-e]isobenzofuran-13-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9953 99.53%
Caco-2 + 0.5484 54.84%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.8606 86.06%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8470 84.70%
OATP1B3 inhibitior + 0.9272 92.72%
MATE1 inhibitior - 0.7000 70.00%
OCT2 inhibitior + 0.5500 55.00%
BSEP inhibitior + 0.9168 91.68%
P-glycoprotein inhibitior + 0.7047 70.47%
P-glycoprotein substrate - 0.7825 78.25%
CYP3A4 substrate + 0.6878 68.78%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9122 91.22%
CYP3A4 inhibition - 0.7564 75.64%
CYP2C9 inhibition - 0.7516 75.16%
CYP2C19 inhibition - 0.8162 81.62%
CYP2D6 inhibition - 0.9226 92.26%
CYP1A2 inhibition - 0.7646 76.46%
CYP2C8 inhibition + 0.4526 45.26%
CYP inhibitory promiscuity - 0.7871 78.71%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.5756 57.56%
Eye corrosion - 0.9886 98.86%
Eye irritation - 0.8927 89.27%
Skin irritation - 0.5700 57.00%
Skin corrosion - 0.9398 93.98%
Ames mutagenesis - 0.7500 75.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8131 81.31%
Micronuclear - 0.6300 63.00%
Hepatotoxicity - 0.6500 65.00%
skin sensitisation - 0.7908 79.08%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity + 0.5145 51.45%
Acute Oral Toxicity (c) III 0.7585 75.85%
Estrogen receptor binding + 0.8286 82.86%
Androgen receptor binding + 0.6504 65.04%
Thyroid receptor binding + 0.6402 64.02%
Glucocorticoid receptor binding + 0.7904 79.04%
Aromatase binding + 0.6637 66.37%
PPAR gamma + 0.8276 82.76%
Honey bee toxicity - 0.7797 77.97%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 1.0000 100.00%

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 98.28% 91.11%
CHEMBL4040 P28482 MAP kinase ERK2 98.28% 83.82%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.09% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.76% 94.45%
CHEMBL2581 P07339 Cathepsin D 91.50% 98.95%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 90.78% 82.69%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.60% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.43% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.86% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.40% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.99% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.82% 89.00%
CHEMBL340 P08684 Cytochrome P450 3A4 86.27% 91.19%
CHEMBL5028 O14672 ADAM10 84.74% 97.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.11% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.67% 99.23%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.41% 97.14%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.46% 92.62%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.45% 93.04%
CHEMBL5255 O00206 Toll-like receptor 4 80.38% 92.50%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 3012494
LOTUS LTS0125353
wikiData Q105246955