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Lolicine A

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 a0945bed-ccb7-41cc-a460-3aebba1d19a6
Taxonomy Organoheterocyclic compounds > Naphthopyrans
IUPAC Name (2S,3S,6S,8S,10R,11R,12R,15S,21R,25R)-10-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,11,22,22,24,24-heptamethyl-7,23-dioxa-31-azaoctacyclo[15.14.0.02,15.03,12.06,11.018,30.019,27.021,25]hentriaconta-1(17),18(30),19(27),28-tetraen-26-one
SMILES (Canonical) CC1(C2CC3=C(C=CC4=C3C5=C(N4)C6(C(C5)CCC7C6(CCC8C7(C(CC(O8)C(C)(C)O)O)C)C)C)C(=O)C2C(O1)(C)C)C
SMILES (Isomeric) C[C@]12CC[C@H]3[C@]([C@@H]1CC[C@@H]4[C@@]2(C5=C(C4)C6=C(N5)C=CC7=C6C[C@@H]8[C@@H](C7=O)C(OC8(C)C)(C)C)C)([C@@H](C[C@H](O3)C(C)(C)O)O)C
InChI InChI=1S/C38H53NO5/c1-33(2,42)28-18-26(40)37(8)25-13-10-19-16-22-29-21-17-23-30(35(5,6)44-34(23,3)4)31(41)20(21)11-12-24(29)39-32(22)38(19,9)36(25,7)15-14-27(37)43-28/h11-12,19,23,25-28,30,39-40,42H,10,13-18H2,1-9H3/t19-,23+,25+,26+,27-,28-,30-,36-,37+,38+/m0/s1
InChI Key LUBQWHCYCGWUJS-GARPVJMRSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C38H53NO5
Molecular Weight 603.80 g/mol
Exact Mass 603.39237379 g/mol
Topological Polar Surface Area (TPSA) 91.80 Ų
XlogP 6.20
Atomic LogP (AlogP) 6.66
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 1

Synonyms

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CHEBI:181404
C20584
(2S,3S,6S,8S,10R,11R,12R,15S,21R,25R)-10-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,11,22,22,24,24-heptamethyl-7,23-dioxa-31-azaoctacyclo[15.14.0.02,15.03,12.06,11.018,30.019,27.021,25]hentriaconta-1(17),18(30),19(27),28-tetraen-26-one

2D Structure

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2D Structure of Lolicine A

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9867 98.67%
Caco-2 - 0.7729 77.29%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.5598 55.98%
OATP2B1 inhibitior - 0.7124 71.24%
OATP1B1 inhibitior + 0.8097 80.97%
OATP1B3 inhibitior + 0.9163 91.63%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.7821 78.21%
BSEP inhibitior + 0.9707 97.07%
P-glycoprotein inhibitior + 0.7737 77.37%
P-glycoprotein substrate + 0.6735 67.35%
CYP3A4 substrate + 0.7218 72.18%
CYP2C9 substrate - 0.8024 80.24%
CYP2D6 substrate - 0.8240 82.40%
CYP3A4 inhibition - 0.8674 86.74%
CYP2C9 inhibition - 0.9446 94.46%
CYP2C19 inhibition - 0.9050 90.50%
CYP2D6 inhibition - 0.9380 93.80%
CYP1A2 inhibition + 0.6585 65.85%
CYP2C8 inhibition + 0.7262 72.62%
CYP inhibitory promiscuity - 0.8805 88.05%
UGT catelyzed + 1.0000 100.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.5597 55.97%
Eye corrosion - 0.9927 99.27%
Eye irritation - 0.9314 93.14%
Skin irritation - 0.7358 73.58%
Skin corrosion - 0.9268 92.68%
Ames mutagenesis + 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6710 67.10%
Micronuclear - 0.6200 62.00%
Hepatotoxicity - 0.6250 62.50%
skin sensitisation - 0.8309 83.09%
Respiratory toxicity + 0.8222 82.22%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity + 0.6058 60.58%
Acute Oral Toxicity (c) III 0.6153 61.53%
Estrogen receptor binding + 0.7609 76.09%
Androgen receptor binding + 0.7316 73.16%
Thyroid receptor binding + 0.5697 56.97%
Glucocorticoid receptor binding + 0.7869 78.69%
Aromatase binding + 0.7173 71.73%
PPAR gamma + 0.6251 62.51%
Honey bee toxicity - 0.7649 76.49%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6100 61.00%
Fish aquatic toxicity + 0.9263 92.63%

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 98.66% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.65% 97.25%
CHEMBL2581 P07339 Cathepsin D 95.75% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.57% 95.56%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 94.53% 93.04%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.02% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.64% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.03% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 92.32% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.05% 96.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 91.21% 95.89%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 88.37% 85.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.10% 86.33%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.02% 94.00%
CHEMBL1902 P62942 FK506-binding protein 1A 86.03% 97.05%
CHEMBL4225 P49760 Dual specificity protein kinase CLK2 85.92% 80.96%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 84.68% 96.77%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.96% 85.14%
CHEMBL2996 Q05655 Protein kinase C delta 83.52% 97.79%
CHEMBL2265 P23141 Acyl coenzyme A:cholesterol acyltransferase 82.78% 85.94%
CHEMBL1937 Q92769 Histone deacetylase 2 82.61% 94.75%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 82.59% 90.93%
CHEMBL3922 P50579 Methionine aminopeptidase 2 82.12% 97.28%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.84% 92.94%
CHEMBL4940 P07195 L-lactate dehydrogenase B chain 81.21% 95.53%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.59% 99.23%
CHEMBL2095226 P05556 Integrin alpha-5/beta-1 80.47% 96.39%

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.
Lolium perenne

Cross-Links

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PubChem 72734310
LOTUS LTS0120489
wikiData Q75052584