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(1S,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'-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 4dd64f06-38b6-43b6-9cc6-f849b7a57e93
Taxonomy Alkaloids and derivatives > Macroline alkaloids
IUPAC Name (1S,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'-one
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C26H32N2O5/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/h4-7,14,16,18-19,21-22,29H,8-13H2,1-3H3/t14-,16-,18-,19+,21+,22+,25+,26-/m1/s1
InChI Key SIUVLTXMJUQAMG-ZIBLNAGFSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C26H32N2O5
Molecular Weight 452.50 g/mol
Exact Mass 452.23112213 g/mol
Topological Polar Surface Area (TPSA) 73.20 Ų
XlogP 1.60
Atomic LogP (AlogP) 2.54
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 1

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,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'-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8734 87.34%
Caco-2 - 0.5946 59.46%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Lysosomes 0.5029 50.29%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8904 89.04%
OATP1B3 inhibitior + 0.9211 92.11%
MATE1 inhibitior - 0.8435 84.35%
OCT2 inhibitior + 0.5500 55.00%
BSEP inhibitior + 0.9160 91.60%
P-glycoprotein inhibitior + 0.5869 58.69%
P-glycoprotein substrate + 0.7399 73.99%
CYP3A4 substrate + 0.7180 71.80%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.6603 66.03%
CYP3A4 inhibition - 0.8537 85.37%
CYP2C9 inhibition - 0.9092 90.92%
CYP2C19 inhibition - 0.7992 79.92%
CYP2D6 inhibition - 0.8973 89.73%
CYP1A2 inhibition - 0.8181 81.81%
CYP2C8 inhibition + 0.5838 58.38%
CYP inhibitory promiscuity - 0.8775 87.75%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6023 60.23%
Eye corrosion - 0.9887 98.87%
Eye irritation - 0.9882 98.82%
Skin irritation - 0.8209 82.09%
Skin corrosion - 0.9507 95.07%
Ames mutagenesis - 0.5224 52.24%
Human Ether-a-go-go-Related Gene inhibition + 0.7233 72.33%
Micronuclear + 0.6000 60.00%
Hepatotoxicity - 0.5125 51.25%
skin sensitisation - 0.8838 88.38%
Respiratory toxicity + 0.8444 84.44%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.8875 88.75%
Nephrotoxicity - 0.6974 69.74%
Acute Oral Toxicity (c) III 0.6487 64.87%
Estrogen receptor binding + 0.8577 85.77%
Androgen receptor binding + 0.7388 73.88%
Thyroid receptor binding + 0.7029 70.29%
Glucocorticoid receptor binding + 0.8540 85.40%
Aromatase binding + 0.8109 81.09%
PPAR gamma + 0.5953 59.53%
Honey bee toxicity - 0.7425 74.25%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity - 0.3628 36.28%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.06% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.41% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.35% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.47% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.45% 89.00%
CHEMBL2581 P07339 Cathepsin D 92.96% 98.95%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 92.58% 99.23%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.52% 97.25%
CHEMBL1951 P21397 Monoamine oxidase A 90.86% 91.49%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.38% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.85% 97.09%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.21% 94.00%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 85.83% 85.11%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 85.05% 100.00%
CHEMBL2996 Q05655 Protein kinase C delta 83.60% 97.79%
CHEMBL5103 Q969S8 Histone deacetylase 10 83.51% 90.08%
CHEMBL2378 P30307 Dual specificity phosphatase Cdc25C 83.50% 96.67%
CHEMBL3192 Q9BY41 Histone deacetylase 8 82.67% 93.99%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 82.44% 95.83%
CHEMBL1937 Q92769 Histone deacetylase 2 82.07% 94.75%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.58% 92.62%
CHEMBL5409 Q8TDU6 G-protein coupled bile acid receptor 1 81.21% 93.65%
CHEMBL3524 P56524 Histone deacetylase 4 80.40% 92.97%
CHEMBL1899 P46098 Serotonin 3a (5-HT3a) receptor 80.25% 100.00%

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 101725662
LOTUS LTS0186251
wikiData Q105254079