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(1S,3'R,5'R,12S,13R,16S,18R,20S,21R)-5'-(hydroxymethyl)-3,16,23-trimethylspiro[15,17-dioxa-3,23-diazahexacyclo[10.10.1.02,10.04,9.013,21.016,20]tricosa-2(10),4,6,8-tetraene-18,2'-oxolane]-3'-ol

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 ae6774be-bfc9-40d1-8644-764cb268d4e7
Taxonomy Alkaloids and derivatives > Macroline alkaloids
IUPAC Name (1S,3'R,5'R,12S,13R,16S,18R,20S,21R)-5'-(hydroxymethyl)-3,16,23-trimethylspiro[15,17-dioxa-3,23-diazahexacyclo[10.10.1.02,10.04,9.013,21.016,20]tricosa-2(10),4,6,8-tetraene-18,2'-oxolane]-3'-ol
SMILES (Canonical) CC12C(CC3(O1)C(CC(O3)CO)O)C4CC5C6=C(CC(C4CO2)N5C)C7=CC=CC=C7N6C
SMILES (Isomeric) C[C@@]12[C@@H](C[C@@]3(O1)[C@@H](C[C@@H](O3)CO)O)[C@@H]4C[C@H]5C6=C(C[C@@H]([C@@H]4CO2)N5C)C7=CC=CC=C7N6C
InChI InChI=1S/C26H34N2O5/c1-25-19(11-26(33-25)23(30)8-14(12-29)32-26)16-9-22-24-17(10-21(27(22)2)18(16)13-31-25)15-6-4-5-7-20(15)28(24)3/h4-7,14,16,18-19,21-23,29-30H,8-13H2,1-3H3/t14-,16-,18-,19+,21+,22+,23-,25+,26-/m1/s1
InChI Key PLQILWGOPQNEFW-DIEFOPEZSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C26H34N2O5
Molecular Weight 454.60 g/mol
Exact Mass 454.24677219 g/mol
Topological Polar Surface Area (TPSA) 76.30 Ų
XlogP 1.60
Atomic LogP (AlogP) 2.33
H-Bond Acceptor 7
H-Bond Donor 2
Rotatable Bonds 1

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,3'R,5'R,12S,13R,16S,18R,20S,21R)-5'-(hydroxymethyl)-3,16,23-trimethylspiro[15,17-dioxa-3,23-diazahexacyclo[10.10.1.02,10.04,9.013,21.016,20]tricosa-2(10),4,6,8-tetraene-18,2'-oxolane]-3'-ol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7584 75.84%
Caco-2 - 0.5786 57.86%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Lysosomes 0.5351 53.51%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8945 89.45%
OATP1B3 inhibitior + 0.9290 92.90%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior + 0.8364 83.64%
P-glycoprotein inhibitior - 0.4787 47.87%
P-glycoprotein substrate + 0.8022 80.22%
CYP3A4 substrate + 0.7176 71.76%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate + 0.3739 37.39%
CYP3A4 inhibition - 0.9204 92.04%
CYP2C9 inhibition - 0.9182 91.82%
CYP2C19 inhibition - 0.8640 86.40%
CYP2D6 inhibition - 0.8928 89.28%
CYP1A2 inhibition - 0.8454 84.54%
CYP2C8 inhibition + 0.6979 69.79%
CYP inhibitory promiscuity - 0.9167 91.67%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5641 56.41%
Eye corrosion - 0.9883 98.83%
Eye irritation - 0.9856 98.56%
Skin irritation - 0.8082 80.82%
Skin corrosion - 0.9452 94.52%
Ames mutagenesis + 0.5676 56.76%
Human Ether-a-go-go-Related Gene inhibition + 0.7859 78.59%
Micronuclear + 0.6500 65.00%
Hepatotoxicity - 0.5039 50.39%
skin sensitisation - 0.8800 88.00%
Respiratory toxicity + 0.8333 83.33%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.9375 93.75%
Nephrotoxicity - 0.7368 73.68%
Acute Oral Toxicity (c) III 0.5814 58.14%
Estrogen receptor binding + 0.8382 83.82%
Androgen receptor binding + 0.7000 70.00%
Thyroid receptor binding + 0.6795 67.95%
Glucocorticoid receptor binding + 0.7395 73.95%
Aromatase binding + 0.7808 78.08%
PPAR gamma + 0.6308 63.08%
Honey bee toxicity - 0.7614 76.14%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity - 0.4917 49.17%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.83% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.91% 89.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.02% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 94.39% 91.49%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.09% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.64% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.45% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 92.29% 85.14%
CHEMBL2581 P07339 Cathepsin D 91.34% 98.95%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 89.65% 94.62%
CHEMBL1914 P06276 Butyrylcholinesterase 88.51% 95.00%
CHEMBL5805 Q9NR97 Toll-like receptor 8 88.43% 96.25%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 86.36% 100.00%
CHEMBL5678 P34947 G protein-coupled receptor kinase 5 86.17% 88.00%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 86.11% 89.44%
CHEMBL3359 P21462 Formyl peptide receptor 1 85.45% 93.56%
CHEMBL5103 Q969S8 Histone deacetylase 10 85.44% 90.08%
CHEMBL2096618 P11274 Bcr/Abl fusion protein 85.05% 85.83%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 85.04% 94.23%
CHEMBL299 P17252 Protein kinase C alpha 84.76% 98.03%
CHEMBL3192 Q9BY41 Histone deacetylase 8 84.56% 93.99%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.01% 86.33%
CHEMBL2996 Q05655 Protein kinase C delta 83.50% 97.79%
CHEMBL226 P30542 Adenosine A1 receptor 80.82% 95.93%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 80.44% 89.62%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 80.32% 95.83%

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.
Alstonia macrophylla

Cross-Links

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PubChem 101262950
LOTUS LTS0162527
wikiData Q105211138