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(3S)-5-[[(1R,3aS,4S,5Z,9R,11R,12aS)-1-(2-acetyloxypropan-2-yl)-4,9,11-trihydroxy-3a-methyl-10-methylidene-1,2,3,4,7,8,9,11,12,12a-decahydrocyclopenta[11]annulen-6-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid

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 6f545c68-a2e8-4faf-bfee-37aa661b0a84
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name (3S)-5-[[(1R,3aS,4S,5Z,9R,11R,12aS)-1-(2-acetyloxypropan-2-yl)-4,9,11-trihydroxy-3a-methyl-10-methylidene-1,2,3,4,7,8,9,11,12,12a-decahydrocyclopenta[11]annulen-6-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
SMILES (Canonical) CC(=O)OC(C)(C)C1CCC2(C1CC(C(=C)C(CCC(=CC2O)COC(=O)CC(C)(CC(=O)O)O)O)O)C
SMILES (Isomeric) CC(=O)OC(C)(C)[C@@H]1CC[C@]2([C@H]1C[C@H](C(=C)[C@@H](CC/C(=C/[C@@H]2O)/COC(=O)C[C@](C)(CC(=O)O)O)O)O)C
InChI InChI=1S/C28H44O10/c1-16-21(30)8-7-18(15-37-25(35)14-27(5,36)13-24(33)34)11-23(32)28(6)10-9-19(20(28)12-22(16)31)26(3,4)38-17(2)29/h11,19-23,30-32,36H,1,7-10,12-15H2,2-6H3,(H,33,34)/b18-11-/t19-,20+,21-,22-,23+,27+,28+/m1/s1
InChI Key FRLDVKJGPODRTR-ZINCXXRESA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H44O10
Molecular Weight 540.60 g/mol
Exact Mass 540.29344760 g/mol
Topological Polar Surface Area (TPSA) 171.00 Ų
XlogP 0.10
Atomic LogP (AlogP) 2.27
H-Bond Acceptor 9
H-Bond Donor 5
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3S)-5-[[(1R,3aS,4S,5Z,9R,11R,12aS)-1-(2-acetyloxypropan-2-yl)-4,9,11-trihydroxy-3a-methyl-10-methylidene-1,2,3,4,7,8,9,11,12,12a-decahydrocyclopenta[11]annulen-6-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9708 97.08%
Caco-2 - 0.7950 79.50%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.7800 78.00%
OATP2B1 inhibitior - 0.5706 57.06%
OATP1B1 inhibitior + 0.8294 82.94%
OATP1B3 inhibitior + 0.8505 85.05%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6525 65.25%
BSEP inhibitior + 0.8619 86.19%
P-glycoprotein inhibitior + 0.5864 58.64%
P-glycoprotein substrate + 0.5189 51.89%
CYP3A4 substrate + 0.7338 73.38%
CYP2C9 substrate - 0.8176 81.76%
CYP2D6 substrate - 0.8786 87.86%
CYP3A4 inhibition - 0.8327 83.27%
CYP2C9 inhibition - 0.6419 64.19%
CYP2C19 inhibition - 0.8824 88.24%
CYP2D6 inhibition - 0.9469 94.69%
CYP1A2 inhibition - 0.8022 80.22%
CYP2C8 inhibition + 0.6588 65.88%
CYP inhibitory promiscuity - 0.9179 91.79%
UGT catelyzed + 0.6362 63.62%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.6845 68.45%
Eye corrosion - 0.9887 98.87%
Eye irritation - 0.9207 92.07%
Skin irritation + 0.5131 51.31%
Skin corrosion - 0.9564 95.64%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7877 78.77%
Micronuclear - 0.8600 86.00%
Hepatotoxicity + 0.5327 53.27%
skin sensitisation - 0.8375 83.75%
Respiratory toxicity + 0.7556 75.56%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity - 0.8569 85.69%
Acute Oral Toxicity (c) I 0.3750 37.50%
Estrogen receptor binding + 0.7704 77.04%
Androgen receptor binding + 0.6653 66.53%
Thyroid receptor binding - 0.5132 51.32%
Glucocorticoid receptor binding + 0.7444 74.44%
Aromatase binding + 0.7179 71.79%
PPAR gamma + 0.5582 55.82%
Honey bee toxicity - 0.6880 68.80%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9944 99.44%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.36% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.18% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.65% 97.25%
CHEMBL2581 P07339 Cathepsin D 94.30% 98.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 92.30% 85.14%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 92.18% 89.05%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.27% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.21% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.55% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 86.19% 82.69%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.83% 95.89%
CHEMBL221 P23219 Cyclooxygenase-1 85.32% 90.17%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 85.08% 94.62%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.60% 95.56%
CHEMBL5028 O14672 ADAM10 83.76% 97.50%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.31% 100.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.07% 99.17%
CHEMBL2179 P04062 Beta-glucocerebrosidase 83.04% 85.31%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.06% 95.89%

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.
Chrozophora plicata

Cross-Links

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PubChem 163070940
LOTUS LTS0125348
wikiData Q105000235