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Presinularolide B

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 2ca33aca-57aa-4149-967c-cd3d5ff60319
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones > Cembranolides
IUPAC Name (3aR,5Z,9E,13E,15R,15aR)-15-hydroxy-6-(hydroxymethyl)-10,14-dimethyl-3-methylidene-3a,4,7,8,11,12,15,15a-octahydrocyclotetradeca[b]furan-2-one
SMILES (Canonical) CC1=CCCC(=CCC2C(C(C(=CCC1)C)O)OC(=O)C2=C)CO
SMILES (Isomeric) C/C/1=C\CC/C(=C/C[C@H]2[C@H]([C@@H](/C(=C/CC1)/C)O)OC(=O)C2=C)/CO
InChI InChI=1S/C20H28O4/c1-13-6-4-8-14(2)18(22)19-17(15(3)20(23)24-19)11-10-16(12-21)9-5-7-13/h7-8,10,17-19,21-22H,3-6,9,11-12H2,1-2H3/b13-7+,14-8+,16-10-/t17-,18-,19-/m1/s1
InChI Key IAWHPIHHKZYGDC-WTDAPOCQSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C20H28O4
Molecular Weight 332.40 g/mol
Exact Mass 332.19875937 g/mol
Topological Polar Surface Area (TPSA) 66.80 Ų
XlogP 1.90
Atomic LogP (AlogP) 3.22
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 1

Synonyms

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(3aR,5Z,9E,13E,15R,15aR)-15-hydroxy-6-(hydroxymethyl)-10,14-dimethyl-3-methylidene-3a,4,7,8,11,12,15,15a-octahydrocyclotetradeca(b)furan-2-one
(3aR,5Z,9E,13E,15R,15aR)-15-hydroxy-6-(hydroxymethyl)-10,14-dimethyl-3-methylidene-3a,4,7,8,11,12,15,15a-octahydrocyclotetradeca[b]furan-2-one
RefChem:175929
1039742-05-6
CHEMBL472333

2D Structure

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2D Structure of Presinularolide B

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9688 96.88%
Caco-2 - 0.5491 54.91%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability + 0.6143 61.43%
Subcellular localzation Mitochondria 0.7040 70.40%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9122 91.22%
OATP1B3 inhibitior + 0.9476 94.76%
MATE1 inhibitior - 0.9212 92.12%
OCT2 inhibitior - 0.5923 59.23%
BSEP inhibitior - 0.7854 78.54%
P-glycoprotein inhibitior - 0.7875 78.75%
P-glycoprotein substrate - 0.8241 82.41%
CYP3A4 substrate + 0.5754 57.54%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8359 83.59%
CYP3A4 inhibition - 0.5511 55.11%
CYP2C9 inhibition - 0.8061 80.61%
CYP2C19 inhibition - 0.8013 80.13%
CYP2D6 inhibition - 0.8520 85.20%
CYP1A2 inhibition + 0.5178 51.78%
CYP2C8 inhibition - 0.7099 70.99%
CYP inhibitory promiscuity - 0.7920 79.20%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6733 67.33%
Eye corrosion - 0.9799 97.99%
Eye irritation - 0.9091 90.91%
Skin irritation - 0.6228 62.28%
Skin corrosion - 0.9390 93.90%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4295 42.95%
Micronuclear - 0.8900 89.00%
Hepatotoxicity + 0.5175 51.75%
skin sensitisation - 0.8284 82.84%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.5667 56.67%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity + 0.6423 64.23%
Acute Oral Toxicity (c) III 0.5192 51.92%
Estrogen receptor binding - 0.5452 54.52%
Androgen receptor binding - 0.4911 49.11%
Thyroid receptor binding - 0.5871 58.71%
Glucocorticoid receptor binding + 0.5819 58.19%
Aromatase binding - 0.6049 60.49%
PPAR gamma - 0.5535 55.35%
Honey bee toxicity - 0.8417 84.17%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6700 67.00%
Fish aquatic toxicity + 0.9896 98.96%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.70% 97.25%
CHEMBL2581 P07339 Cathepsin D 92.34% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.77% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.27% 95.56%
CHEMBL218 P21554 Cannabinoid CB1 receptor 85.18% 96.61%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 84.16% 95.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.07% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.78% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.59% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 81.43% 96.09%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 80.71% 90.71%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.11% 99.23%

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.
There are no matching plants.

Cross-Links

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PubChem 24899657
LOTUS LTS0228826
wikiData Q105036311