(-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde 7,18,20-acetal

Details

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Internal ID 0b68d2a7-1997-4ac6-b7bf-9f88c2bdc0c4
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name (1R,5S,8R,10S,17S)-5-methyl-13-propan-2-yl-7,9-dioxapentacyclo[8.6.2.01,8.05,17.011,16]octadeca-11,13,15-trien-14-ol
SMILES (Canonical) CC(C)C1=C(C=C2C(=C1)C3CC4C25CCCC4(COC5O3)C)O
SMILES (Isomeric) CC(C)C1=C(C=C2C(=C1)[C@@H]3C[C@@H]4[C@]25CCC[C@@]4(CO[C@@H]5O3)C)O
InChI InChI=1S/C20H26O3/c1-11(2)12-7-13-14(8-15(12)21)20-6-4-5-19(3)10-22-18(20)23-16(13)9-17(19)20/h7-8,11,16-18,21H,4-6,9-10H2,1-3H3/t16-,17-,18+,19+,20-/m0/s1
InChI Key PNHPVNJXLPYREE-OMZCGLGVSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H26O3
Molecular Weight 314.40 g/mol
Exact Mass 314.18819469 g/mol
Topological Polar Surface Area (TPSA) 38.70 Ų
XlogP 4.10
Atomic LogP (AlogP) 4.39
H-Bond Acceptor 3
H-Bond Donor 1
Rotatable Bonds 1

Synonyms

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(-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde 7,18,20-acetal
CHEMBL1651066
Q27138890
(7alpha,20S)-7,20:18,20-Diepoxyabieta-8,11,13-trien-12-ol
(5S,6aS,9S,12aR,13S)-9-methyl-3-(propan-2-yl)-9,10,11,12-tetrahydro-5H,6aH,8H-9,12a,5-(ethane[1,1,2]triyl)oxocino[2,3-c][2]benzopyran-2-ol

2D Structure

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2D Structure of (-)-(4S,5S,7S,10R,20S)-7,12,18-trihydroxyabieta-8,11,13-trien-20-aldehyde 7,18,20-acetal

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9864 98.64%
Caco-2 + 0.8129 81.29%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.8433 84.33%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8844 88.44%
OATP1B3 inhibitior + 0.9267 92.67%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior - 0.6812 68.12%
P-glycoprotein inhibitior - 0.7851 78.51%
P-glycoprotein substrate - 0.6786 67.86%
CYP3A4 substrate + 0.6273 62.73%
CYP2C9 substrate - 0.6000 60.00%
CYP2D6 substrate - 0.6671 66.71%
CYP3A4 inhibition - 0.8406 84.06%
CYP2C9 inhibition - 0.8436 84.36%
CYP2C19 inhibition - 0.8052 80.52%
CYP2D6 inhibition - 0.9087 90.87%
CYP1A2 inhibition - 0.6252 62.52%
CYP2C8 inhibition - 0.6146 61.46%
CYP inhibitory promiscuity - 0.9396 93.96%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9000 90.00%
Carcinogenicity (trinary) Non-required 0.6843 68.43%
Eye corrosion - 0.9891 98.91%
Eye irritation - 0.9054 90.54%
Skin irritation - 0.8115 81.15%
Skin corrosion - 0.9648 96.48%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4446 44.46%
Micronuclear - 0.8741 87.41%
Hepatotoxicity - 0.5423 54.23%
skin sensitisation - 0.8351 83.51%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.5333 53.33%
Mitochondrial toxicity - 0.6000 60.00%
Nephrotoxicity - 0.7097 70.97%
Acute Oral Toxicity (c) III 0.6323 63.23%
Estrogen receptor binding + 0.6846 68.46%
Androgen receptor binding + 0.6149 61.49%
Thyroid receptor binding + 0.7865 78.65%
Glucocorticoid receptor binding + 0.6260 62.60%
Aromatase binding - 0.5472 54.72%
PPAR gamma + 0.8292 82.92%
Honey bee toxicity - 0.8254 82.54%
Biodegradation - 0.9750 97.50%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9779 97.79%

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 99.39% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.61% 94.45%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 91.90% 90.71%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.57% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.35% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 89.01% 97.25%
CHEMBL2581 P07339 Cathepsin D 88.94% 98.95%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 88.33% 99.15%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 87.10% 95.71%
CHEMBL284 P27487 Dipeptidyl peptidase IV 86.87% 95.69%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 85.33% 85.11%
CHEMBL241 Q14432 Phosphodiesterase 3A 84.73% 92.94%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 84.64% 100.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 84.56% 91.07%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.06% 95.56%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 83.82% 89.62%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 83.47% 96.77%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.03% 92.62%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.85% 93.56%
CHEMBL4444 P04070 Vitamin K-dependent protein C 82.62% 93.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.49% 86.33%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 82.23% 90.24%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.47% 100.00%
CHEMBL4208 P20618 Proteasome component C5 81.27% 90.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.56% 89.00%
CHEMBL3192 Q9BY41 Histone deacetylase 8 80.36% 93.99%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 80.01% 92.88%

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.
Fraxinus sieboldiana

Cross-Links

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PubChem 53326127
LOTUS LTS0044741
wikiData Q27138890