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(3S,3aR,6S,6aS)-6-[(E)-5-[(1S,2R,4aR,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enyl]-3,6,6a-trihydroxy-3,3a-dihydro-2H-furo[3,2-b]furan-5-one

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

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Internal ID da35d0e3-d098-4c0a-86eb-a27cf5d1a8de
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
IUPAC Name (3S,3aR,6S,6aS)-6-[(E)-5-[(1S,2R,4aR,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enyl]-3,6,6a-trihydroxy-3,3a-dihydro-2H-furo[3,2-b]furan-5-one
SMILES (Canonical) CC1CCC2(C(C1(C)CCC(=CCC3(C(=O)OC4C3(OCC4O)O)O)C)CCC=C2C)C
SMILES (Isomeric) C[C@@H]1CC[C@@]2([C@H]([C@@]1(C)CC/C(=C/C[C@]3(C(=O)O[C@H]4[C@@]3(OC[C@@H]4O)O)O)/C)CCC=C2C)C
InChI InChI=1S/C26H40O6/c1-16(10-14-25(29)22(28)32-21-19(27)15-31-26(21,25)30)9-12-23(4)18(3)11-13-24(5)17(2)7-6-8-20(23)24/h7,10,18-21,27,29-30H,6,8-9,11-15H2,1-5H3/b16-10+/t18-,19+,20+,21-,23+,24+,25-,26+/m1/s1
InChI Key GUGKETBJPXLNIM-DASHNJABSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C26H40O6
Molecular Weight 448.60 g/mol
Exact Mass 448.28248899 g/mol
Topological Polar Surface Area (TPSA) 96.20 Ų
XlogP 4.40
Atomic LogP (AlogP) 3.64
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3S,3aR,6S,6aS)-6-[(E)-5-[(1S,2R,4aR,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enyl]-3,6,6a-trihydroxy-3,3a-dihydro-2H-furo[3,2-b]furan-5-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9396 93.96%
Caco-2 - 0.6518 65.18%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.7728 77.28%
OATP2B1 inhibitior - 0.7179 71.79%
OATP1B1 inhibitior + 0.8862 88.62%
OATP1B3 inhibitior + 0.9403 94.03%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.6750 67.50%
BSEP inhibitior + 0.6134 61.34%
P-glycoprotein inhibitior - 0.5184 51.84%
P-glycoprotein substrate - 0.5767 57.67%
CYP3A4 substrate + 0.6779 67.79%
CYP2C9 substrate - 0.7950 79.50%
CYP2D6 substrate - 0.8579 85.79%
CYP3A4 inhibition - 0.8640 86.40%
CYP2C9 inhibition - 0.9017 90.17%
CYP2C19 inhibition - 0.9166 91.66%
CYP2D6 inhibition - 0.9491 94.91%
CYP1A2 inhibition - 0.9253 92.53%
CYP2C8 inhibition + 0.4512 45.12%
CYP inhibitory promiscuity - 0.9361 93.61%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.4770 47.70%
Eye corrosion - 0.9925 99.25%
Eye irritation - 0.9452 94.52%
Skin irritation + 0.6912 69.12%
Skin corrosion - 0.9387 93.87%
Ames mutagenesis - 0.5237 52.37%
Human Ether-a-go-go-Related Gene inhibition - 0.5438 54.38%
Micronuclear - 0.9000 90.00%
Hepatotoxicity - 0.5250 52.50%
skin sensitisation - 0.9035 90.35%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity - 0.5555 55.55%
Acute Oral Toxicity (c) III 0.4193 41.93%
Estrogen receptor binding + 0.6923 69.23%
Androgen receptor binding + 0.7305 73.05%
Thyroid receptor binding + 0.6542 65.42%
Glucocorticoid receptor binding + 0.7694 76.94%
Aromatase binding + 0.6574 65.74%
PPAR gamma + 0.5639 56.39%
Honey bee toxicity - 0.7762 77.62%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9808 98.08%

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
CHEMBL4040 P28482 MAP kinase ERK2 98.84% 83.82%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.91% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.42% 91.11%
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 92.26% 83.57%
CHEMBL2581 P07339 Cathepsin D 91.48% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.64% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.69% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.56% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.85% 97.09%
CHEMBL325 Q13547 Histone deacetylase 1 86.26% 95.92%
CHEMBL1937 Q92769 Histone deacetylase 2 85.12% 94.75%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 82.96% 94.80%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 82.76% 96.09%
CHEMBL1871 P10275 Androgen Receptor 82.60% 96.43%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.01% 86.33%
CHEMBL3401 O75469 Pregnane X receptor 81.80% 94.73%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.28% 92.94%
CHEMBL5103 Q969S8 Histone deacetylase 10 80.95% 90.08%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.64% 99.23%
CHEMBL1902 P62942 FK506-binding protein 1A 80.39% 97.05%

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.
Brachyglottis bidwillii

Cross-Links

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PubChem 163102320
LOTUS LTS0077948
wikiData Q105020118