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(1R,4aS,5S,6R,7R,8S,8aR)-7-acetyloxy-8-benzoyloxy-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethylspiro[3,4,5,7,8,8a-hexahydro-2H-naphthalene-6,2'-oxirane]-1-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 0c9e751d-8a11-43e9-9e85-4b55436d0a7d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name (1R,4aS,5S,6R,7R,8S,8aR)-7-acetyloxy-8-benzoyloxy-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethylspiro[3,4,5,7,8,8a-hexahydro-2H-naphthalene-6,2'-oxirane]-1-carboxylic acid
SMILES (Canonical) CC(=CCO)CCC1C2(CCCC(C2C(C(C13CO3)OC(=O)C)OC(=O)C4=CC=CC=C4)(C)C(=O)O)C
SMILES (Isomeric) C/C(=C\CO)/CC[C@H]1[C@]2(CCC[C@@]([C@@H]2[C@@H]([C@H]([C@]13CO3)OC(=O)C)OC(=O)C4=CC=CC=C4)(C)C(=O)O)C
InChI InChI=1S/C29H38O8/c1-18(13-16-30)11-12-21-27(3)14-8-15-28(4,26(33)34)23(27)22(24(36-19(2)31)29(21)17-35-29)37-25(32)20-9-6-5-7-10-20/h5-7,9-10,13,21-24,30H,8,11-12,14-17H2,1-4H3,(H,33,34)/b18-13+/t21-,22-,23+,24+,27+,28+,29-/m0/s1
InChI Key AELDBPDJBONNBN-YEXSUBDNSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C29H38O8
Molecular Weight 514.60 g/mol
Exact Mass 514.25666817 g/mol
Topological Polar Surface Area (TPSA) 123.00 Ų
XlogP 4.40
Atomic LogP (AlogP) 4.16
H-Bond Acceptor 7
H-Bond Donor 2
Rotatable Bonds 8

Synonyms

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BDBM50046955

2D Structure

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2D Structure of (1R,4aS,5S,6R,7R,8S,8aR)-7-acetyloxy-8-benzoyloxy-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethylspiro[3,4,5,7,8,8a-hexahydro-2H-naphthalene-6,2'-oxirane]-1-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 + 0.9447 94.47%
Caco-2 - 0.6614 66.14%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.7717 77.17%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7986 79.86%
OATP1B3 inhibitior + 0.8344 83.44%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6548 65.48%
BSEP inhibitior + 0.9650 96.50%
P-glycoprotein inhibitior + 0.8068 80.68%
P-glycoprotein substrate - 0.6521 65.21%
CYP3A4 substrate + 0.6426 64.26%
CYP2C9 substrate - 0.8105 81.05%
CYP2D6 substrate - 0.8734 87.34%
CYP3A4 inhibition - 0.5180 51.80%
CYP2C9 inhibition - 0.6357 63.57%
CYP2C19 inhibition - 0.6868 68.68%
CYP2D6 inhibition - 0.9087 90.87%
CYP1A2 inhibition - 0.5529 55.29%
CYP2C8 inhibition + 0.7757 77.57%
CYP inhibitory promiscuity - 0.7715 77.15%
UGT catelyzed - 0.9000 90.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6288 62.88%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.9405 94.05%
Skin irritation - 0.6668 66.68%
Skin corrosion - 0.9583 95.83%
Ames mutagenesis - 0.7102 71.02%
Human Ether-a-go-go-Related Gene inhibition + 0.8828 88.28%
Micronuclear - 0.7200 72.00%
Hepatotoxicity - 0.7466 74.66%
skin sensitisation - 0.8672 86.72%
Respiratory toxicity + 0.5778 57.78%
Reproductive toxicity + 0.8000 80.00%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity - 0.5637 56.37%
Acute Oral Toxicity (c) III 0.4654 46.54%
Estrogen receptor binding + 0.7591 75.91%
Androgen receptor binding + 0.6565 65.65%
Thyroid receptor binding + 0.5560 55.60%
Glucocorticoid receptor binding + 0.7670 76.70%
Aromatase binding + 0.6090 60.90%
PPAR gamma + 0.6294 62.94%
Honey bee toxicity - 0.8839 88.39%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9964 99.64%

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 97.63% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 95.46% 90.17%
CHEMBL2581 P07339 Cathepsin D 95.27% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.27% 86.33%
CHEMBL4040 P28482 MAP kinase ERK2 93.45% 83.82%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.24% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.18% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.94% 99.23%
CHEMBL1951 P21397 Monoamine oxidase A 87.24% 91.49%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.18% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.07% 95.89%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 85.83% 83.00%
CHEMBL340 P08684 Cytochrome P450 3A4 85.67% 91.19%
CHEMBL5028 O14672 ADAM10 85.49% 97.50%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 85.21% 94.62%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 84.38% 91.07%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 83.66% 82.69%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 83.58% 93.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.86% 100.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.49% 95.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.84% 100.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.48% 92.62%

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.
Scoparia dulcis

Cross-Links

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PubChem 118707631
LOTUS LTS0010909
wikiData Q104910130