PlantaeDB Logo
Login Sign-up

[(1S,2R,4aS,8S,8aR)-2,8-diacetyloxy-5-(3,5-dihydroxy-3-methylpentyl)-1,4a,6-trimethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]methyl acetate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

Top
Internal ID 5fe0bdf4-652b-4f62-a8d8-1a26d78af6fd
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name [(1S,2R,4aS,8S,8aR)-2,8-diacetyloxy-5-(3,5-dihydroxy-3-methylpentyl)-1,4a,6-trimethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]methyl acetate
SMILES (Canonical) CC1=C(C2(CCC(C(C2C(C1=O)OC(=O)C)(C)COC(=O)C)OC(=O)C)C)CCC(C)(CCO)O
SMILES (Isomeric) CC1=C([C@]2(CC[C@H]([C@]([C@@H]2[C@@H](C1=O)OC(=O)C)(C)COC(=O)C)OC(=O)C)C)CCC(C)(CCO)O
InChI InChI=1S/C26H40O9/c1-15-19(8-10-24(5,32)12-13-27)25(6)11-9-20(34-17(3)29)26(7,14-33-16(2)28)23(25)22(21(15)31)35-18(4)30/h20,22-23,27,32H,8-14H2,1-7H3/t20-,22-,23-,24?,25-,26+/m1/s1
InChI Key XMJCMUGHDGHZBN-FNMNNZMESA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C26H40O9
Molecular Weight 496.60 g/mol
Exact Mass 496.26723285 g/mol
Topological Polar Surface Area (TPSA) 136.00 Ų
XlogP 1.90
Atomic LogP (AlogP) 2.65
H-Bond Acceptor 9
H-Bond Donor 2
Rotatable Bonds 9

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(1S,2R,4aS,8S,8aR)-2,8-diacetyloxy-5-(3,5-dihydroxy-3-methylpentyl)-1,4a,6-trimethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]methyl acetate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9374 93.74%
Caco-2 - 0.5575 55.75%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.8329 83.29%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8261 82.61%
OATP1B3 inhibitior + 0.8089 80.89%
MATE1 inhibitior - 0.7400 74.00%
OCT2 inhibitior - 0.5890 58.90%
BSEP inhibitior + 0.8281 82.81%
P-glycoprotein inhibitior + 0.7239 72.39%
P-glycoprotein substrate - 0.6098 60.98%
CYP3A4 substrate + 0.6866 68.66%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9180 91.80%
CYP3A4 inhibition - 0.8268 82.68%
CYP2C9 inhibition - 0.8677 86.77%
CYP2C19 inhibition - 0.8891 88.91%
CYP2D6 inhibition - 0.9423 94.23%
CYP1A2 inhibition - 0.9089 90.89%
CYP2C8 inhibition + 0.5503 55.03%
CYP inhibitory promiscuity - 0.9424 94.24%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7207 72.07%
Eye corrosion - 0.9928 99.28%
Eye irritation - 0.8806 88.06%
Skin irritation - 0.5216 52.16%
Skin corrosion - 0.9666 96.66%
Ames mutagenesis - 0.6900 69.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5186 51.86%
Micronuclear - 0.8100 81.00%
Hepatotoxicity - 0.5625 56.25%
skin sensitisation - 0.9202 92.02%
Respiratory toxicity - 0.5222 52.22%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity + 0.6017 60.17%
Acute Oral Toxicity (c) III 0.6811 68.11%
Estrogen receptor binding + 0.8019 80.19%
Androgen receptor binding + 0.6448 64.48%
Thyroid receptor binding - 0.5268 52.68%
Glucocorticoid receptor binding + 0.7500 75.00%
Aromatase binding + 0.6498 64.98%
PPAR gamma + 0.7887 78.87%
Honey bee toxicity - 0.8388 83.88%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.9814 98.14%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.60% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.95% 96.09%
CHEMBL2581 P07339 Cathepsin D 92.85% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.33% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.34% 97.09%
CHEMBL4040 P28482 MAP kinase ERK2 88.61% 83.82%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 87.92% 100.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.87% 94.45%
CHEMBL2996 Q05655 Protein kinase C delta 86.14% 97.79%
CHEMBL3437 Q16853 Amine oxidase, copper containing 86.05% 94.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.12% 86.33%
CHEMBL2782 P35610 Acyl coenzyme A:cholesterol acyltransferase 1 85.07% 91.65%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.81% 89.00%
CHEMBL1937 Q92769 Histone deacetylase 2 84.10% 94.75%
CHEMBL5028 O14672 ADAM10 83.69% 97.50%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 83.50% 89.05%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.41% 95.56%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.18% 92.62%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.18% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.89% 100.00%
CHEMBL5255 O00206 Toll-like receptor 4 81.89% 92.50%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.79% 97.14%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.54% 82.69%
CHEMBL340 P08684 Cytochrome P450 3A4 80.48% 91.19%

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.
Leonurus macranthus

Cross-Links

Top
PubChem 122187012
LOTUS LTS0019465
wikiData Q105331136