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methyl (E)-4-[(1R,2S,4R,4aR,6S,8aS)-4,6-dihydroxy-5,5,8a-trimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]-2-[(2R)-oxiran-2-yl]but-2-enoate

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 e709372d-399d-463a-947b-61d3077a3a7a
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name methyl (E)-4-[(1R,2S,4R,4aR,6S,8aS)-4,6-dihydroxy-5,5,8a-trimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]-2-[(2R)-oxiran-2-yl]but-2-enoate
SMILES (Canonical) CC1(C(CCC2(C1C(CC3(C2CC=C(C4CO4)C(=O)OC)CO3)O)C)O)C
SMILES (Isomeric) C[C@]12CC[C@@H](C([C@@H]1[C@@H](C[C@]3([C@@H]2C/C=C(\[C@@H]4CO4)/C(=O)OC)CO3)O)(C)C)O
InChI InChI=1S/C21H32O6/c1-19(2)16(23)7-8-20(3)15(21(11-27-21)9-13(22)17(19)20)6-5-12(14-10-26-14)18(24)25-4/h5,13-17,22-23H,6-11H2,1-4H3/b12-5+/t13-,14+,15-,16+,17+,20-,21-/m1/s1
InChI Key OCZNPNYYEDNTIA-KKPOYHGYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H32O6
Molecular Weight 380.50 g/mol
Exact Mass 380.21988874 g/mol
Topological Polar Surface Area (TPSA) 91.80 Ų
XlogP 1.60
Atomic LogP (AlogP) 1.83
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (E)-4-[(1R,2S,4R,4aR,6S,8aS)-4,6-dihydroxy-5,5,8a-trimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]-2-[(2R)-oxiran-2-yl]but-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9665 96.65%
Caco-2 + 0.5354 53.54%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.8126 81.26%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8881 88.81%
OATP1B3 inhibitior + 0.8987 89.87%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.7250 72.50%
BSEP inhibitior + 0.8608 86.08%
P-glycoprotein inhibitior - 0.7183 71.83%
P-glycoprotein substrate - 0.5000 50.00%
CYP3A4 substrate + 0.7099 70.99%
CYP2C9 substrate - 0.8129 81.29%
CYP2D6 substrate - 0.8669 86.69%
CYP3A4 inhibition - 0.8396 83.96%
CYP2C9 inhibition - 0.7234 72.34%
CYP2C19 inhibition - 0.7812 78.12%
CYP2D6 inhibition - 0.9367 93.67%
CYP1A2 inhibition - 0.7968 79.68%
CYP2C8 inhibition - 0.6342 63.42%
CYP inhibitory promiscuity - 0.9236 92.36%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5674 56.74%
Eye corrosion - 0.9891 98.91%
Eye irritation - 0.9587 95.87%
Skin irritation - 0.6879 68.79%
Skin corrosion - 0.9527 95.27%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5283 52.83%
Micronuclear - 0.7000 70.00%
Hepatotoxicity - 0.7250 72.50%
skin sensitisation - 0.8044 80.44%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity + 0.5553 55.53%
Acute Oral Toxicity (c) III 0.3916 39.16%
Estrogen receptor binding + 0.8576 85.76%
Androgen receptor binding + 0.6177 61.77%
Thyroid receptor binding + 0.6828 68.28%
Glucocorticoid receptor binding + 0.8602 86.02%
Aromatase binding + 0.7456 74.56%
PPAR gamma + 0.7016 70.16%
Honey bee toxicity - 0.6921 69.21%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9725 97.25%

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 97.25% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.33% 96.09%
CHEMBL1914 P06276 Butyrylcholinesterase 95.66% 95.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.43% 94.45%
CHEMBL226 P30542 Adenosine A1 receptor 90.99% 95.93%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 90.17% 94.33%
CHEMBL3922 P50579 Methionine aminopeptidase 2 88.99% 97.28%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 88.17% 96.38%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.63% 97.09%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 86.50% 95.50%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 85.84% 85.14%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 85.26% 98.75%
CHEMBL340 P08684 Cytochrome P450 3A4 84.94% 91.19%
CHEMBL204 P00734 Thrombin 84.43% 96.01%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 84.18% 82.69%
CHEMBL5028 O14672 ADAM10 83.77% 97.50%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 83.54% 91.24%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.44% 100.00%
CHEMBL221 P23219 Cyclooxygenase-1 83.25% 90.17%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.83% 91.07%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 81.93% 95.71%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.84% 92.62%
CHEMBL4005 P42336 PI3-kinase p110-alpha subunit 81.32% 97.47%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 81.15% 89.05%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 80.76% 97.50%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.36% 97.14%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 80.02% 89.34%

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.
Aframomum zambesiacum

Cross-Links

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PubChem 163009583
LOTUS LTS0162092
wikiData Q105189664