[(3S,4aR,5S,6R,6aR,10aS,10bR)-5-acetyloxy-4a,6a,10b-trimethyl-7-methylidene-2',8-dioxospiro[2,5,6,10a-tetrahydro-1H-benzo[f]chromene-3,4'-oxolane]-6-yl] acetate

Details

Top
Internal ID ff25d406-68ef-44cb-8b05-9df484576ba4
Taxonomy Organoheterocyclic compounds > Naphthopyrans
IUPAC Name [(3S,4aR,5S,6R,6aR,10aS,10bR)-5-acetyloxy-4a,6a,10b-trimethyl-7-methylidene-2',8-dioxospiro[2,5,6,10a-tetrahydro-1H-benzo[f]chromene-3,4'-oxolane]-6-yl] acetate
SMILES (Canonical) CC(=O)OC1C(C2(C(CCC3(O2)CC(=O)OC3)(C4C1(C(=C)C(=O)C=C4)C)C)C)OC(=O)C
SMILES (Isomeric) CC(=O)O[C@H]1[C@@H]([C@]2([C@](CC[C@]3(O2)CC(=O)OC3)([C@@H]4[C@@]1(C(=C)C(=O)C=C4)C)C)C)OC(=O)C
InChI InChI=1S/C24H30O8/c1-13-16(27)7-8-17-21(4)9-10-24(11-18(28)29-12-24)32-23(21,6)20(31-15(3)26)19(22(13,17)5)30-14(2)25/h7-8,17,19-20H,1,9-12H2,2-6H3/t17-,19+,20+,21-,22+,23+,24+/m1/s1
InChI Key JUSZHGHKALHJHU-YDCCHNKESA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C24H30O8
Molecular Weight 446.50 g/mol
Exact Mass 446.19406791 g/mol
Topological Polar Surface Area (TPSA) 105.00 Ų
XlogP 2.00
Atomic LogP (AlogP) 2.44
H-Bond Acceptor 8
H-Bond Donor 0
Rotatable Bonds 2

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(3S,4aR,5S,6R,6aR,10aS,10bR)-5-acetyloxy-4a,6a,10b-trimethyl-7-methylidene-2',8-dioxospiro[2,5,6,10a-tetrahydro-1H-benzo[f]chromene-3,4'-oxolane]-6-yl] acetate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9803 98.03%
Caco-2 - 0.5913 59.13%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.7863 78.63%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8674 86.74%
OATP1B3 inhibitior + 0.8726 87.26%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior + 0.5600 56.00%
P-glycoprotein inhibitior + 0.7071 70.71%
P-glycoprotein substrate - 0.7012 70.12%
CYP3A4 substrate + 0.6498 64.98%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9014 90.14%
CYP3A4 inhibition - 0.5740 57.40%
CYP2C9 inhibition - 0.8953 89.53%
CYP2C19 inhibition - 0.8908 89.08%
CYP2D6 inhibition - 0.9371 93.71%
CYP1A2 inhibition - 0.6573 65.73%
CYP2C8 inhibition + 0.5334 53.34%
CYP inhibitory promiscuity - 0.8216 82.16%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5364 53.64%
Eye corrosion - 0.9848 98.48%
Eye irritation - 0.8872 88.72%
Skin irritation - 0.5132 51.32%
Skin corrosion - 0.8718 87.18%
Ames mutagenesis - 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6840 68.40%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.5372 53.72%
skin sensitisation - 0.8324 83.24%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity - 0.5000 50.00%
Nephrotoxicity + 0.6859 68.59%
Acute Oral Toxicity (c) III 0.5114 51.14%
Estrogen receptor binding + 0.7810 78.10%
Androgen receptor binding + 0.6195 61.95%
Thyroid receptor binding + 0.6140 61.40%
Glucocorticoid receptor binding + 0.7888 78.88%
Aromatase binding + 0.7828 78.28%
PPAR gamma + 0.5720 57.20%
Honey bee toxicity - 0.6972 69.72%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.7050 70.50%
Fish aquatic toxicity + 0.9890 98.90%

Targets

Top

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 98.17% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.41% 94.45%
CHEMBL2581 P07339 Cathepsin D 94.41% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.66% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.56% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.76% 95.56%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 90.30% 96.77%
CHEMBL340 P08684 Cytochrome P450 3A4 85.02% 91.19%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.80% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.60% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.16% 86.33%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.84% 95.50%
CHEMBL3864 Q06124 Protein-tyrosine phosphatase 2C 83.56% 94.42%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.39% 89.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.34% 91.07%
CHEMBL3922 P50579 Methionine aminopeptidase 2 80.93% 97.28%

Plants that contains it

Top
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.
Scutellaria barbata

Cross-Links

Top
PubChem 162878698
LOTUS LTS0216421
wikiData Q105135397