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(1R,7aR,9S,11bR)-1-acetyloxy-9-[(S)-furan-3-yl(hydroxy)methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxospiro[2,5a,6,10,11,11a-hexahydro-1H-naphtho[2,1-c]oxepine-8,3'-oxirane]-2'-carboxylic 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 e9f32060-30ec-4340-8c04-da08173796c2
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
IUPAC Name (1R,7aR,9S,11bR)-1-acetyloxy-9-[(S)-furan-3-yl(hydroxy)methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxospiro[2,5a,6,10,11,11a-hexahydro-1H-naphtho[2,1-c]oxepine-8,3'-oxirane]-2'-carboxylic acid
SMILES (Canonical) CC(=O)OC1CC(=O)OC(C2C1(C3CCC(C4(C3(C(=O)C2)C)C(O4)C(=O)O)(C)C(C5=COC=C5)O)C)(C)C
SMILES (Isomeric) CC(=O)O[C@@H]1CC(=O)OC(C2[C@]1(C3CC[C@@](C4([C@@]3(C(=O)C2)C)C(O4)C(=O)O)(C)[C@H](C5=COC=C5)O)C)(C)C
InChI InChI=1S/C28H36O10/c1-14(29)36-19-12-20(31)37-24(2,3)17-11-18(30)27(6)16(26(17,19)5)7-9-25(4,21(32)15-8-10-35-13-15)28(27)22(38-28)23(33)34/h8,10,13,16-17,19,21-22,32H,7,9,11-12H2,1-6H3,(H,33,34)/t16?,17?,19-,21+,22?,25+,26-,27+,28?/m1/s1
InChI Key MYIIZRCOTDMMDC-TYSZJBGBSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H36O10
Molecular Weight 532.60 g/mol
Exact Mass 532.23084734 g/mol
Topological Polar Surface Area (TPSA) 153.00 Ų
XlogP 1.80
Atomic LogP (AlogP) 3.21
H-Bond Acceptor 9
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 (1R,7aR,9S,11bR)-1-acetyloxy-9-[(S)-furan-3-yl(hydroxy)methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxospiro[2,5a,6,10,11,11a-hexahydro-1H-naphtho[2,1-c]oxepine-8,3'-oxirane]-2'-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9559 95.59%
Caco-2 - 0.7366 73.66%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.7483 74.83%
OATP2B1 inhibitior - 0.8608 86.08%
OATP1B1 inhibitior + 0.7693 76.93%
OATP1B3 inhibitior - 0.2911 29.11%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.7071 70.71%
BSEP inhibitior + 0.8138 81.38%
P-glycoprotein inhibitior + 0.7062 70.62%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.6810 68.10%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8420 84.20%
CYP3A4 inhibition - 0.5439 54.39%
CYP2C9 inhibition - 0.7081 70.81%
CYP2C19 inhibition - 0.7432 74.32%
CYP2D6 inhibition - 0.9392 93.92%
CYP1A2 inhibition - 0.6936 69.36%
CYP2C8 inhibition + 0.6672 66.72%
CYP inhibitory promiscuity - 0.9156 91.56%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5185 51.85%
Eye corrosion - 0.9906 99.06%
Eye irritation - 0.8454 84.54%
Skin irritation - 0.6610 66.10%
Skin corrosion - 0.8734 87.34%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4044 40.44%
Micronuclear - 0.6600 66.00%
Hepatotoxicity - 0.6750 67.50%
skin sensitisation - 0.8454 84.54%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity + 0.8125 81.25%
Nephrotoxicity + 0.4762 47.62%
Acute Oral Toxicity (c) III 0.3470 34.70%
Estrogen receptor binding + 0.8044 80.44%
Androgen receptor binding + 0.7990 79.90%
Thyroid receptor binding + 0.6536 65.36%
Glucocorticoid receptor binding + 0.8145 81.45%
Aromatase binding + 0.8019 80.19%
PPAR gamma + 0.6940 69.40%
Honey bee toxicity - 0.7426 74.26%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5850 58.50%
Fish aquatic toxicity + 0.9867 98.67%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.81% 85.14%
CHEMBL2581 P07339 Cathepsin D 98.18% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.47% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.29% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.10% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.72% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.55% 99.23%
CHEMBL340 P08684 Cytochrome P450 3A4 87.80% 91.19%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.49% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.32% 95.89%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 85.80% 94.62%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 85.69% 93.04%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.24% 86.33%
CHEMBL3524 P56524 Histone deacetylase 4 85.05% 92.97%
CHEMBL1937 Q92769 Histone deacetylase 2 84.87% 94.75%
CHEMBL221 P23219 Cyclooxygenase-1 83.09% 90.17%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 82.88% 94.08%
CHEMBL5028 O14672 ADAM10 82.66% 97.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.80% 97.09%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 81.74% 100.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.12% 94.00%

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.
Citrus × aurantium

Cross-Links

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PubChem 101359992
LOTUS LTS0156866
wikiData Q105174937