(1S)-2alpha,7beta,13alpha-Triacetoxy-9alpha-(benzoyloxy)-11,15-seco-1,11-cyclotaxa-4(20),11-diene-5alpha,10beta,15-triol

Details

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Internal ID cdb7da05-b179-4501-b06a-ed22e6fa7325
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Taxanes and derivatives
IUPAC Name [(2S,4R,5R,5aS,6S,8S,9aR,10S,10aS)-2,6,10-triacetyloxy-4,8-dihydroxy-10a-(2-hydroxypropan-2-yl)-3,5a-dimethyl-9-methylidene-2,4,5,6,7,8,9a,10-octahydro-1H-benzo[g]azulen-5-yl] benzoate
SMILES (Canonical) CC1=C2C(C(C3(C(CC(C(=C)C3C(C2(CC1OC(=O)C)C(C)(C)O)OC(=O)C)O)OC(=O)C)C)OC(=O)C4=CC=CC=C4)O
SMILES (Isomeric) CC1=C2[C@H]([C@@H]([C@@]3([C@H](C[C@@H](C(=C)[C@H]3[C@@H]([C@@]2(C[C@@H]1OC(=O)C)C(C)(C)O)OC(=O)C)O)OC(=O)C)C)OC(=O)C4=CC=CC=C4)O
InChI InChI=1S/C33H42O11/c1-16-22(37)14-24(42-19(4)35)32(8)26(16)28(43-20(5)36)33(31(6,7)40)15-23(41-18(3)34)17(2)25(33)27(38)29(32)44-30(39)21-12-10-9-11-13-21/h9-13,22-24,26-29,37-38,40H,1,14-15H2,2-8H3/t22-,23-,24-,26-,27+,28-,29-,32+,33-/m0/s1
InChI Key YWYQRZNXOIULGT-JGYXPHOZSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C33H42O11
Molecular Weight 614.70 g/mol
Exact Mass 614.27271215 g/mol
Topological Polar Surface Area (TPSA) 166.00 Ų
XlogP 1.30
Atomic LogP (AlogP) 2.80
H-Bond Acceptor 11
H-Bond Donor 3
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S)-2alpha,7beta,13alpha-Triacetoxy-9alpha-(benzoyloxy)-11,15-seco-1,11-cyclotaxa-4(20),11-diene-5alpha,10beta,15-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9919 99.19%
Caco-2 - 0.7948 79.48%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.7277 72.77%
OATP2B1 inhibitior - 0.7104 71.04%
OATP1B1 inhibitior + 0.8602 86.02%
OATP1B3 inhibitior - 0.2262 22.62%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior + 0.8255 82.55%
P-glycoprotein inhibitior + 0.7852 78.52%
P-glycoprotein substrate + 0.5382 53.82%
CYP3A4 substrate + 0.6806 68.06%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8683 86.83%
CYP3A4 inhibition - 0.6813 68.13%
CYP2C9 inhibition - 0.6953 69.53%
CYP2C19 inhibition - 0.7042 70.42%
CYP2D6 inhibition - 0.8883 88.83%
CYP1A2 inhibition - 0.7128 71.28%
CYP2C8 inhibition + 0.8122 81.22%
CYP inhibitory promiscuity - 0.8283 82.83%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5709 57.09%
Eye corrosion - 0.9902 99.02%
Eye irritation - 0.9014 90.14%
Skin irritation - 0.5742 57.42%
Skin corrosion - 0.9246 92.46%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4354 43.54%
Micronuclear - 0.5800 58.00%
Hepatotoxicity + 0.5459 54.59%
skin sensitisation - 0.6545 65.45%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity + 0.4616 46.16%
Acute Oral Toxicity (c) III 0.3759 37.59%
Estrogen receptor binding + 0.7373 73.73%
Androgen receptor binding + 0.7057 70.57%
Thyroid receptor binding + 0.5588 55.88%
Glucocorticoid receptor binding + 0.7217 72.17%
Aromatase binding + 0.6236 62.36%
PPAR gamma + 0.7201 72.01%
Honey bee toxicity - 0.6665 66.65%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9971 99.71%

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
CHEMBL1951 P21397 Monoamine oxidase A 98.36% 91.49%
CHEMBL2581 P07339 Cathepsin D 98.05% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.07% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.00% 96.09%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 92.79% 95.50%
CHEMBL221 P23219 Cyclooxygenase-1 91.58% 90.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.50% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.28% 95.56%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 87.77% 94.62%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 87.64% 97.14%
CHEMBL340 P08684 Cytochrome P450 3A4 83.72% 91.19%
CHEMBL2535 P11166 Glucose transporter 83.48% 98.75%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.03% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.69% 89.00%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 82.00% 81.11%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 81.71% 82.69%
CHEMBL253 P34972 Cannabinoid CB2 receptor 81.64% 97.25%
CHEMBL5028 O14672 ADAM10 81.14% 97.50%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.98% 93.56%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.17% 91.07%

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.
Equisetum hyemale
Taxus mairei

Cross-Links

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PubChem 5315698
NPASS NPC38394
LOTUS LTS0269240
wikiData Q105367437