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(2R)-3-{(2R)-4-[{(1S,2R,4aS,6R,8S,8aR)-2-[(2E)-but-2-en-2-yl]-6,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl}(hydroxy)methylidene]-3,5-dioxopyrrolidin-2-yl}-2-hydroxy-2-methylpropanoic 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 138ef0c3-ad22-4724-9bf1-94348b377859
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
IUPAC Name (2R)-3-[(2R,4Z)-4-[[(1S,2R,4aS,6R,8S,8aR)-2-[(E)-but-2-en-2-yl]-6,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-hydroxymethylidene]-3,5-dioxopyrrolidin-2-yl]-2-hydroxy-2-methylpropanoic acid
SMILES (Canonical) CC=C(C)C1C=CC2CC(CC(C2C1C(=C3C(=O)C(NC3=O)CC(C)(C(=O)O)O)O)C)C
SMILES (Isomeric) C/C=C(\C)/[C@@H]1C=C[C@@H]2C[C@@H](C[C@@H]([C@H]2[C@@H]1/C(=C/3\C(=O)[C@H](NC3=O)C[C@](C)(C(=O)O)O)/O)C)C
InChI InChI=1S/C25H35NO6/c1-6-13(3)16-8-7-15-10-12(2)9-14(4)18(15)19(16)22(28)20-21(27)17(26-23(20)29)11-25(5,32)24(30)31/h6-8,12,14-19,28,32H,9-11H2,1-5H3,(H,26,29)(H,30,31)/b13-6+,22-20-/t12-,14+,15-,16+,17-,18-,19-,25-/m1/s1
InChI Key AVZATKWNGXCSDN-FRNHIKLPSA-N
Popularity 4 references in papers

Physical and Chemical Properties

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Molecular Formula C25H35NO6
Molecular Weight 445.50 g/mol
Exact Mass 445.24643784 g/mol
Topological Polar Surface Area (TPSA) 124.00 Ų
XlogP 4.50
Atomic LogP (AlogP) 3.16
H-Bond Acceptor 5
H-Bond Donor 4
Rotatable Bonds 5

Synonyms

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(2R)-3-{(2R)-4-[{(1S,2R,4aS,6R,8S,8aR)-2-[(2E)-but-2-en-2-yl]-6,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl}(hydroxy)methylidene]-3,5-dioxopyrrolidin-2-yl}-2-hydroxy-2-methylpropanoic acid
CHEBI:68749
Sch 210792
Q27137162
(2R)-3-[(2R,4Z)-4-[[(1S,2R,4aS,6R,8S,8aR)-6,8-dimethyl-2-[(E)-1-methylprop-1-enyl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-hydroxy-methylene]-3,5-dioxo-pyrrolidin-2-yl]-2-hydroxy-2-methyl-propanoic acid
2-Pyrrolidinepropanoic acid, .alpha.-hydroxy-4-[hydroxy[(1S,2R,4aS,6R,8S,8aR)-1,2,4a,5,6,7,8,8a-octahydro-6,8-dimethyl-2-[(1E)-1-methyl-1-propenyl]-1-naphthalenyl]methylene]-.alpha.-methyl-3,5-dioxo-, (.alpha.R,2R,4Z)-

2D Structure

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2D Structure of (2R)-3-{(2R)-4-[{(1S,2R,4aS,6R,8S,8aR)-2-[(2E)-but-2-en-2-yl]-6,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl}(hydroxy)methylidene]-3,5-dioxopyrrolidin-2-yl}-2-hydroxy-2-methylpropanoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9561 95.61%
Caco-2 - 0.7600 76.00%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Plasma membrane 0.4377 43.77%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8332 83.32%
OATP1B3 inhibitior + 0.9321 93.21%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.8298 82.98%
P-glycoprotein inhibitior - 0.6163 61.63%
P-glycoprotein substrate + 0.5995 59.95%
CYP3A4 substrate + 0.6100 61.00%
CYP2C9 substrate - 0.8035 80.35%
CYP2D6 substrate - 0.8973 89.73%
CYP3A4 inhibition - 0.9687 96.87%
CYP2C9 inhibition - 0.8856 88.56%
CYP2C19 inhibition - 0.8886 88.86%
CYP2D6 inhibition - 0.9451 94.51%
CYP1A2 inhibition - 0.9125 91.25%
CYP2C8 inhibition - 0.6433 64.33%
CYP inhibitory promiscuity - 0.7994 79.94%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.4581 45.81%
Eye corrosion - 0.9900 99.00%
Eye irritation - 0.9677 96.77%
Skin irritation - 0.7338 73.38%
Skin corrosion - 0.9343 93.43%
Ames mutagenesis - 0.5554 55.54%
Human Ether-a-go-go-Related Gene inhibition - 0.7165 71.65%
Micronuclear + 0.7600 76.00%
Hepatotoxicity + 0.6000 60.00%
skin sensitisation - 0.8386 83.86%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity - 0.7010 70.10%
Acute Oral Toxicity (c) III 0.4105 41.05%
Estrogen receptor binding + 0.6571 65.71%
Androgen receptor binding + 0.7018 70.18%
Thyroid receptor binding + 0.6396 63.96%
Glucocorticoid receptor binding + 0.7443 74.43%
Aromatase binding - 0.4894 48.94%
PPAR gamma + 0.6884 68.84%
Honey bee toxicity - 0.7930 79.30%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.7997 79.97%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 99.32% 97.25%
CHEMBL4040 P28482 MAP kinase ERK2 99.03% 83.82%
CHEMBL2581 P07339 Cathepsin D 97.15% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.88% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.78% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.19% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.13% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.37% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.33% 97.09%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 83.32% 90.93%
CHEMBL3976 Q9UHL4 Dipeptidyl peptidase II 81.75% 92.29%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 80.28% 89.34%
CHEMBL3401 O75469 Pregnane X receptor 80.12% 94.73%

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.
There are no matching plants.

Cross-Links

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PubChem 54683155
LOTUS LTS0130072
wikiData Q27137162