Heliotrine, N-oxide

Details

• Internal ID: 510df944-0b0e-4011-9835-c9b12733f590
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(7S,8S)-7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl]methyl 2-hydroxy-2-(1-methoxyethyl)-3-methylbutanoate
• SMILES (Canonical): CC(C)C(C(C)OC)(C(=O)OCC1=CC[N+]2(C1C(CC2)O)[O-])O
• SMILES (Isomeric): CC(C)C(C(C)OC)(C(=O)OCC1=CC[N+]2([C@@H]1[C@H](CC2)O)[O-])O
• InChI: InChI=1S/C16H27NO6/c1-10(2)16(20,11(3)22-4)15(19)23-9-12-5-7-17(21)8-6-13(18)14(12)17/h5,10-11,13-14,18,20H,6-9H2,1-4H3/t11?,13-,14-,16?,17?/m0/s1
• InChI Key: QSTHEUSPIBEICI-ORJSOOTCSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₇NO₆
• Molecular Weight: 329.39 g/mol
• Exact Mass: 329.18383758 g/mol
• Topological Polar Surface Area (TPSA): 94.10 Ų
• XlogP: -0.50

Synonyms

• [(7S,8S)-7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl]methyl 2-hydroxy-2-(1-methoxyethyl)-3-methylbutanoate
• Heliotrine, N-oxide
• [(7S,8R)-7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate
• NSC 30621
• Heliotrine-N-oxide
• (1S-(1alpha,7(2R*,3S*),7aalpha))-2-Hydroxy-2-(1-methoxyethyl)-3-methylbutanoic acid, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester
• Butanoic acid, 2-hydroxy-2-(1-methoxyethyl)-3-methyl-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, N-oxide, (1S-(1-alpha,7(2R*,3S*),7a-alpha))-
• Butanoic acid, 2-hydroxy-3-methoxy-2-(1-methylethyl)-, [(1S,7aS)-2,3,5,7a-tetrahydro-1-hydroxy-4-oxido-1H-pyrrolizin-7-yl]methyl ester

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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.69%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.88%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.85%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.52%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.61%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.50%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.12%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.55%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.74%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.52%	94.45%

Plants that contains it

• Heliotropium dasycarpum
• Heliotropium disciforme
• Heliotropium dissitiflorum

Cross-Links

• PubChem: 22581
• LOTUS: LTS0241668
• wikiData: Q82962942