Heliotrine

Details

• Internal ID: e95d1c12-aa83-471e-b624-8a0c7f4f9445
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate
• SMILES (Canonical): CC(C)C(C(C)OC)(C(=O)OCC1=CCN2C1C(CC2)O)O
• SMILES (Isomeric): C[C@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@H](CC2)O)O)OC
• InChI: InChI=1S/C16H27NO5/c1-10(2)16(20,11(3)21-4)15(19)22-9-12-5-7-17-8-6-13(18)14(12)17/h5,10-11,13-14,18,20H,6-9H2,1-4H3/t11-,13+,14-,16+/m1/s1
• InChI Key: LMFKRLGHEKVMNT-UJDVCPFMSA-N
• Popularity: 288 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₇NO₅
• Molecular Weight: 313.39 g/mol
• Exact Mass: 313.18892296 g/mol
• Topological Polar Surface Area (TPSA): 79.20 Ų
• XlogP: 0.10

Synonyms

• 303-33-3
• 7S-Heliotrine
• (+)-Heliotrine
• Heliotron
• CCRIS 9196
• AI3-51769
• ZYB88Y4FUZ
• CHEBI:5643
• Butanoic acid, 2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methyl-, [(1S,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S)-
• Butanoic acid, 2-hydroxy-2-((1R)-1-methoxyethyl)-3-methyl-, ((1S,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (2S)-
• ((1S,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl (2S,3R)-2-hydroxy-2-isopropyl-3-methoxybutanoate
• UNII-ZYB88Y4FUZ
• BRN 0292841
• 9-Heliotrylheliotridine
• HELIOTRINE, (+)-
• CHEMBL2165593
• DTXSID3075381
• LMFKRLGHEKVMNT-UJDVCPFMSA-N
• Heliotrine 100 microg/mL in Water
• MFCD00213991
• AKOS030495261
• [(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate
• 1ST14163
• AI351769
• AI3 51769
• HY-126128
• CS-0090611
• J-017913
• Q27106845
• (2S)-2-Hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoic Acid [(1S,7aR)-2,3,5,7a-Tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl Ester
• [(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S,3R)-2-hydroxy-2-isopropyl-3-methoxy-butanoate
• [1S-[1alpha,7[R*(S*)],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, (1S-(1 alpha,7(2R*,3S*),7a alpha))-
• BUTANOIC ACID, 2-HYDROXY-2-(1-METHOXYETHYL)-3-METHYL-, (2,3,5,7A-TETRAHYDRO-1-HYDROXY-1H-PYRROLIZIN-7-YL)METHYL ESTER, (1S-(1.ALPHA.,7(R*(S*)),7A.ALPHA.))-
• Butanoic acid, 2-hydroxy-2-(1-methoxyethyl)-3-methyl-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, [1S-[1?,7[R*(S*)],7a?]]-; Heliotrine (6CI,8CI); (+)-Heliotrine; 7S-Heliotrine

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	99.44%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.59%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.91%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.86%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.25%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.62%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.07%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.97%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.65%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.94%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.10%	100.00%

Plants that contains it

• Heliotropium acutiflorum
• Heliotropium bacciferum
• Heliotropium dasycarpum
• Heliotropium disciforme
• Heliotropium dissitiflorum
• Heliotropium europaeum
• Heliotropium indicum
• Heliotropium lasiocarpum
• Heliotropium olgae
• Heliotropium suaveolens
• Heliotropium subulatum
• Moltkiopsis ciliata

Cross-Links

• PubChem: 906426
• LOTUS: LTS0168475
• wikiData: Q27106845