Retrorsine N-oxide

Details

• Internal ID: 8e0ba691-0cf9-43fc-96d7-3df8c5c50829
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: (1R,4Z,6R,7S,14S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
• SMILES (Canonical): CC=C1CC(C(C(=O)OCC2=CC[N+]3(C2C(CC3)OC1=O)[O-])(CO)O)C
• SMILES (Isomeric): C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CC[N@@+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(CO)O)C
• InChI: InChI=1S/C18H25NO7/c1-3-12-8-11(2)18(23,10-20)17(22)25-9-13-4-6-19(24)7-5-14(15(13)19)26-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-/t11-,14-,15-,18-,19-/m1/s1
• InChI Key: IDIMIWQPUHURPV-BJODLBMNSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₅NO₇
• Molecular Weight: 367.40 g/mol
• Exact Mass: 367.16310214 g/mol
• Topological Polar Surface Area (TPSA): 111.00 Ų
• XlogP: 0.00

Synonyms

• Retrorsine, N-oxide
• Retrorsine N-oxide
• ISATIDINE
• 51819GRV4U
• cis-Retronecic acid ester of retronecine-N-oxide
• Senecionan-11,16-dione, 12,18-dihydroxy-, 4-oxide
• Retrorsine-N-oxide
• 15503-86-3
• UNII-51819GRV4U
• CCRIS 4339
• HSDB 3499
• BRN 0058804
• ISATIDINE [IARC]
• 12,18-Dihydroxysenecionan-11,16-dione 4-oxide
• 12,18-Dihydroxysenecionan-11,16-dione-4-oxide
• 4-27-00-06664 (Beilstein Handbook Reference)
• trans-15-Ethylidene-12beta-hydroxy-12alpha-hydroxymethyl-13beta-methylsenec-1-enine-4-oxide
• 12,18-DIHYDROXYSENECIONAN-11,16-DIONE-4-OXIDE [HSDB]
• (1,6)DIOXACYCLODODECINO(2,3,4-GH)PYRROLIZINE-2,7-DIONE, 3- ETHYLIDENE-3,4,5,6,9,11,13,14,14A,14B-DECAHYDRO-6-HYDROXY-6- (HYDROXYMETHYL)-5-METHYL-, 14-OXIDE, (3Z,5R,6S,14AR,14BR)-
• (1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, 14-oxide, (3Z,5R,6S,14aR,14bR)-
• 15-ETHYLIDENE-12.BETA.-HYDROXY-12.ALPHA.-HYDROXYMETHYL- 13.BETA.-METHYLSENEC-1-ENINE-4-OXIDE, TRANS-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.59%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.79%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.37%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.71%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.58%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.85%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.06%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.22%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.89%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.61%	99.23%

Plants that contains it

• Petasites hybridus
• Senecio brasiliensis
• Senecio latifolius
• Senecio riddellii
• Werneria nubigena
• Xenophyllum decorum

Cross-Links

• PubChem: 76972338
• LOTUS: LTS0153932
• wikiData: Q104388529