Lampranthin II

Details

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Internal ID 8904cfcd-63cb-43e9-a318-bea167be444d
Taxonomy Alkaloids and derivatives > Betalains > Betacyanins and derivatives
IUPAC Name (2S)-1-[(2E)-2-[(2S)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene]-6-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-2,3-dihydroindol-1-ium-2-carboxylate
SMILES (Canonical) COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(C(O2)OC3=C(C=C4C(=C3)CC([N+]4=CC=C5CC(NC(=C5)C(=O)O)C(=O)O)C(=O)[O-])O)O)O)O)O
SMILES (Isomeric) COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(C=C4C(=C3)C[C@H]([N+]4=C/C=C/5\C[C@H](NC(=C5)C(=O)O)C(=O)O)C(=O)[O-])O)O)O)O)O
InChI InChI=1S/C34H34N2O16/c1-49-24-10-15(2-4-22(24)37)3-5-27(39)50-14-26-28(40)29(41)30(42)34(52-26)51-25-12-17-11-21(33(47)48)36(20(17)13-23(25)38)7-6-16-8-18(31(43)44)35-19(9-16)32(45)46/h2-8,10,12-13,19,21,26,28-30,34,40-42H,9,11,14H2,1H3,(H5,37,38,39,43,44,45,46,47,48)/t19-,21-,26+,28+,29-,30+,34+/m0/s1
InChI Key BRMDRKOAVZEJCS-WPUGSIMNSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C34H34N2O16
Molecular Weight 726.60 g/mol
Exact Mass 726.19083300 g/mol
Topological Polar Surface Area (TPSA) 285.00 Ų
XlogP 0.90
Atomic LogP (AlogP) -1.72
H-Bond Acceptor 15
H-Bond Donor 8
Rotatable Bonds 11

Synonyms

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32074-65-0
C08552
(2S)-1-[(2E)-2-[(2S)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene]-6-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-2,3-dihydroindol-1-ium-2-carboxylate
CHEBI:6368
DTXSID10474612
Q27107169
(2S)-1-[(2E)-2-[(2S)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene]-6-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoyl]oxymethyl]tetrahydropyran-2-yl]oxy-indolin-1-ium-2-carboxylate

2D Structure

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2D Structure of Lampranthin II

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.7233 72.33%
Caco-2 - 0.8811 88.11%
Blood Brain Barrier - 0.7250 72.50%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Nucleus 0.4035 40.35%
OATP2B1 inhibitior - 0.5708 57.08%
OATP1B1 inhibitior + 0.8314 83.14%
OATP1B3 inhibitior + 0.9331 93.31%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.8361 83.61%
BSEP inhibitior + 0.7802 78.02%
P-glycoprotein inhibitior + 0.7204 72.04%
P-glycoprotein substrate + 0.6920 69.20%
CYP3A4 substrate + 0.7077 70.77%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8499 84.99%
CYP3A4 inhibition - 0.8161 81.61%
CYP2C9 inhibition - 0.7334 73.34%
CYP2C19 inhibition - 0.7362 73.62%
CYP2D6 inhibition - 0.7830 78.30%
CYP1A2 inhibition - 0.6536 65.36%
CYP2C8 inhibition + 0.8211 82.11%
CYP inhibitory promiscuity - 0.7847 78.47%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.4809 48.09%
Eye corrosion - 0.9842 98.42%
Eye irritation - 0.9127 91.27%
Skin irritation - 0.7806 78.06%
Skin corrosion - 0.9309 93.09%
Ames mutagenesis - 0.6023 60.23%
Human Ether-a-go-go-Related Gene inhibition + 0.7101 71.01%
Micronuclear + 0.8800 88.00%
Hepatotoxicity - 0.8300 83.00%
skin sensitisation - 0.8399 83.99%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9375 93.75%
Nephrotoxicity - 0.9456 94.56%
Acute Oral Toxicity (c) III 0.6297 62.97%
Estrogen receptor binding + 0.7956 79.56%
Androgen receptor binding + 0.6654 66.54%
Thyroid receptor binding + 0.5635 56.35%
Glucocorticoid receptor binding + 0.6238 62.38%
Aromatase binding + 0.5801 58.01%
PPAR gamma + 0.7018 70.18%
Honey bee toxicity - 0.7229 72.29%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.8831 88.31%

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 98.60% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.22% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 98.15% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 95.51% 96.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 94.32% 99.17%
CHEMBL2581 P07339 Cathepsin D 90.94% 98.95%
CHEMBL3194 P02766 Transthyretin 90.81% 90.71%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.53% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.38% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.25% 95.56%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 90.01% 89.62%
CHEMBL2535 P11166 Glucose transporter 89.98% 98.75%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.39% 95.89%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 87.69% 90.71%
CHEMBL241 Q14432 Phosphodiesterase 3A 83.69% 92.94%
CHEMBL4040 P28482 MAP kinase ERK2 83.24% 83.82%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.98% 100.00%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 82.02% 91.71%
CHEMBL226 P30542 Adenosine A1 receptor 80.99% 95.93%

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.
Beta vulgaris
Lampranthus bicolor
Lampranthus sociorum
Phytolacca americana
Ullucus tuberosus

Cross-Links

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PubChem 11953909
LOTUS LTS0020822
wikiData Q27107169