[(1S,2S,6R,10S,11R,13S,14R,15R)-13-[(4Z,7Z)-deca-4,7-dienoyl]oxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] benzoate

Details

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Internal ID e9aa1731-0a45-4956-8f12-f9c498a16046
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tigliane and ingenane diterpenoids > Phorbol esters
IUPAC Name [(1S,2S,6R,10S,11R,13S,14R,15R)-13-[(4Z,7Z)-deca-4,7-dienoyl]oxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] benzoate
SMILES (Canonical) CCC=CCC=CCCC(=O)OC12C(C1(C)C)C3C=C(CC4(C(C3(C(C2OC(=O)C5=CC=CC=C5)C)O)C=C(C4=O)C)O)CO
SMILES (Isomeric) CC/C=C\C/C=C\CCC(=O)O[C@@]12[C@@H](C1(C)C)[C@@H]3C=C(C[C@]4([C@H]([C@]3([C@@H]([C@H]2OC(=O)C5=CC=CC=C5)C)O)C=C(C4=O)C)O)CO
InChI InChI=1S/C37H46O8/c1-6-7-8-9-10-11-15-18-29(39)45-37-30(34(37,4)5)27-20-25(22-38)21-35(42)28(19-23(2)31(35)40)36(27,43)24(3)32(37)44-33(41)26-16-13-12-14-17-26/h7-8,10-14,16-17,19-20,24,27-28,30,32,38,42-43H,6,9,15,18,21-22H2,1-5H3/b8-7-,11-10-/t24-,27+,28-,30-,32-,35-,36-,37-/m1/s1
InChI Key HCPYBGDUUHWAPM-SKMAVYCASA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C37H46O8
Molecular Weight 618.80 g/mol
Exact Mass 618.31926842 g/mol
Topological Polar Surface Area (TPSA) 130.00 Ų
XlogP 4.60
Atomic LogP (AlogP) 5.04
H-Bond Acceptor 8
H-Bond Donor 3
Rotatable Bonds 10

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,2S,6R,10S,11R,13S,14R,15R)-13-[(4Z,7Z)-deca-4,7-dienoyl]oxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] benzoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9764 97.64%
Caco-2 - 0.8293 82.93%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.7981 79.81%
OATP2B1 inhibitior - 0.5720 57.20%
OATP1B1 inhibitior + 0.7629 76.29%
OATP1B3 inhibitior + 0.9157 91.57%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.6818 68.18%
BSEP inhibitior + 0.9417 94.17%
P-glycoprotein inhibitior + 0.8338 83.38%
P-glycoprotein substrate + 0.6442 64.42%
CYP3A4 substrate + 0.6944 69.44%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9126 91.26%
CYP3A4 inhibition - 0.7533 75.33%
CYP2C9 inhibition + 0.7076 70.76%
CYP2C19 inhibition - 0.7821 78.21%
CYP2D6 inhibition - 0.8945 89.45%
CYP1A2 inhibition - 0.8217 82.17%
CYP2C8 inhibition + 0.7742 77.42%
CYP inhibitory promiscuity - 0.6497 64.97%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6927 69.27%
Eye corrosion - 0.9916 99.16%
Eye irritation - 0.9237 92.37%
Skin irritation - 0.6197 61.97%
Skin corrosion - 0.9521 95.21%
Ames mutagenesis - 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8239 82.39%
Micronuclear - 0.7000 70.00%
Hepatotoxicity - 0.5750 57.50%
skin sensitisation - 0.8457 84.57%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.9778 97.78%
Mitochondrial toxicity + 0.8625 86.25%
Nephrotoxicity - 0.8744 87.44%
Acute Oral Toxicity (c) III 0.5154 51.54%
Estrogen receptor binding + 0.7866 78.66%
Androgen receptor binding + 0.7159 71.59%
Thyroid receptor binding + 0.6401 64.01%
Glucocorticoid receptor binding + 0.7926 79.26%
Aromatase binding + 0.6472 64.72%
PPAR gamma + 0.7123 71.23%
Honey bee toxicity - 0.8177 81.77%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9907 99.07%

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
CHEMBL2581 P07339 Cathepsin D 97.70% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.90% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.22% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.09% 95.56%
CHEMBL2996 Q05655 Protein kinase C delta 92.66% 97.79%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 92.58% 99.23%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.99% 97.25%
CHEMBL221 P23219 Cyclooxygenase-1 90.45% 90.17%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 88.25% 91.07%
CHEMBL4208 P20618 Proteasome component C5 88.07% 90.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.97% 99.17%
CHEMBL218 P21554 Cannabinoid CB1 receptor 83.76% 96.61%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 83.74% 93.00%
CHEMBL5028 O14672 ADAM10 83.11% 97.50%
CHEMBL299 P17252 Protein kinase C alpha 82.66% 98.03%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.38% 97.09%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 81.12% 91.71%
CHEMBL3192 Q9BY41 Histone deacetylase 8 80.63% 93.99%

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.
Stellera chamaejasme

Cross-Links

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PubChem 71712508
NPASS NPC22571
ChEMBL CHEMBL2375487