[(1aR,3aR,4R,5R,5'R,7R,7aR,7bS)-5'-(furan-3-yl)-3a-hydroxy-5,7a,7b-trimethyl-2'-oxospiro[1a,2,3,5,6,7-hexahydronaphtho[1,2-b]oxirene-4,3'-oxolane]-7-yl] (Z)-2-methylbut-2-enoate

Details

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Internal ID 399bd8e3-f6bb-45d8-90f2-f6c1c307528d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
IUPAC Name [(1aR,3aR,4R,5R,5'R,7R,7aR,7bS)-5'-(furan-3-yl)-3a-hydroxy-5,7a,7b-trimethyl-2'-oxospiro[1a,2,3,5,6,7-hexahydronaphtho[1,2-b]oxirene-4,3'-oxolane]-7-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1CC(C2(CC(OC2=O)C3=COC=C3)C4(C1(C5(C(O5)CC4)C)C)O)C
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@@H]1C[C@H]([C@]2(C[C@@H](OC2=O)C3=COC=C3)[C@@]4([C@@]1([C@]5([C@H](O5)CC4)C)C)O)C
InChI InChI=1S/C25H32O7/c1-6-14(2)20(26)31-19-11-15(3)24(12-17(30-21(24)27)16-8-10-29-13-16)25(28)9-7-18-23(5,32-18)22(19,25)4/h6,8,10,13,15,17-19,28H,7,9,11-12H2,1-5H3/b14-6-/t15-,17-,18-,19-,22+,23-,24+,25-/m1/s1
InChI Key SFRFAFNPUPGNPG-IGNITQPSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C25H32O7
Molecular Weight 444.50 g/mol
Exact Mass 444.21480336 g/mol
Topological Polar Surface Area (TPSA) 98.50 Ų
XlogP 3.00
Atomic LogP (AlogP) 3.86
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1aR,3aR,4R,5R,5'R,7R,7aR,7bS)-5'-(furan-3-yl)-3a-hydroxy-5,7a,7b-trimethyl-2'-oxospiro[1a,2,3,5,6,7-hexahydronaphtho[1,2-b]oxirene-4,3'-oxolane]-7-yl] (Z)-2-methylbut-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 + 0.9927 99.27%
Caco-2 - 0.5760 57.60%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.7648 76.48%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7535 75.35%
OATP1B3 inhibitior - 0.2947 29.47%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.8571 85.71%
BSEP inhibitior + 0.8732 87.32%
P-glycoprotein inhibitior + 0.6212 62.12%
P-glycoprotein substrate + 0.5986 59.86%
CYP3A4 substrate + 0.6974 69.74%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8746 87.46%
CYP3A4 inhibition + 0.6312 63.12%
CYP2C9 inhibition - 0.6516 65.16%
CYP2C19 inhibition - 0.7308 73.08%
CYP2D6 inhibition - 0.9389 93.89%
CYP1A2 inhibition - 0.6381 63.81%
CYP2C8 inhibition + 0.5236 52.36%
CYP inhibitory promiscuity - 0.8452 84.52%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.4886 48.86%
Eye corrosion - 0.9911 99.11%
Eye irritation - 0.9376 93.76%
Skin irritation - 0.5880 58.80%
Skin corrosion - 0.9176 91.76%
Ames mutagenesis - 0.5640 56.40%
Human Ether-a-go-go-Related Gene inhibition + 0.8597 85.97%
Micronuclear - 0.5900 59.00%
Hepatotoxicity + 0.7042 70.42%
skin sensitisation - 0.8373 83.73%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.9250 92.50%
Nephrotoxicity + 0.4767 47.67%
Acute Oral Toxicity (c) I 0.4122 41.22%
Estrogen receptor binding + 0.9070 90.70%
Androgen receptor binding + 0.7019 70.19%
Thyroid receptor binding + 0.6897 68.97%
Glucocorticoid receptor binding + 0.8329 83.29%
Aromatase binding + 0.7437 74.37%
PPAR gamma + 0.6042 60.42%
Honey bee toxicity - 0.7643 76.43%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6800 68.00%
Fish aquatic toxicity + 1.0000 100.00%

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 96.77% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.92% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.49% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.22% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.03% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.58% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.21% 86.33%
CHEMBL221 P23219 Cyclooxygenase-1 89.03% 90.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.20% 99.23%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.26% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.85% 100.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.11% 95.50%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.11% 97.14%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.87% 94.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 81.75% 97.25%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 81.27% 82.69%

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.
Microglossa pyrrhopappa

Cross-Links

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PubChem 163019523
LOTUS LTS0263757
wikiData Q105251972