(+)-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
• 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: 313 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
• Atomic LogP (AlogP): 0.33
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 303-33-3
• (+)-Heliotrine
• 7S-Heliotrine
• ZYB88Y4FUZ
• 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)-
• DTXSID3075381
• [(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate
• 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)-
• ((7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl (2S)-2-hydroxy-2-((1R)-1-methoxyethyl)-3-methylbutanoate
• ((7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl (2S,3R)-2-hydroxy-2-isopropyl-3-methoxy-butanoate
• [(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S,3R)-2-hydroxy-2-isopropyl-3-methoxy-butanoate
• RefChem:783494
• DTXCID6038166
• Heliotron
• CCRIS 9196
• AI3-51769
• UNII-ZYB88Y4FUZ
• BRN 0292841
• 9-Heliotrylheliotridine
• HELIOTRINE, (+)-
• CHEBI:5643
• orb1705587
• orb3140682
• CHEMBL2165593
• SCHEMBL30580759
• LMFKRLGHEKVMNT-UJDVCPFMSA-N
• MSK14163
• Heliotrine 100 microg/mL in Water
• MFCD00213991
• AKOS030495261
• ((1S,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl (2S,3R)-2-hydroxy-2-isopropyl-3-methoxybutanoate
• FH161602
• HY-126128
• CS-0090611
• NS00098506
• T20523
• 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
• (2S,3R)-((1S,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl 2-hydroxy-2-isopropyl-3-methoxybutanoate
• [(1S,7aR)-1-Hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S,3R)-2-hydroxy-3-methoxy-2-(propan-2-yl)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.))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9017	90.17%
Caco-2	+	0.6522	65.22%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6992	69.92%
OATP2B1 inhibitior	-	0.8533	85.33%
OATP1B1 inhibitior	+	0.9059	90.59%
OATP1B3 inhibitior	+	0.9417	94.17%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6808	68.08%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	+	0.5095	50.95%
CYP3A4 substrate	+	0.5814	58.14%
CYP2C9 substrate	-	0.8067	80.67%
CYP2D6 substrate	+	0.3521	35.21%
CYP3A4 inhibition	-	0.9807	98.07%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9110	91.10%
CYP2D6 inhibition	-	0.5929	59.29%
CYP1A2 inhibition	-	0.9048	90.48%
CYP2C8 inhibition	-	0.8623	86.23%
CYP inhibitory promiscuity	-	0.9609	96.09%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Danger	0.6393	63.93%
Eye corrosion	-	0.9812	98.12%
Eye irritation	-	0.9775	97.75%
Skin irritation	-	0.7597	75.97%
Skin corrosion	-	0.9152	91.52%
Ames mutagenesis	+	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7355	73.55%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	+	1.0000	100.00%
skin sensitisation	-	0.8188	81.88%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.4870	48.70%
Acute Oral Toxicity (c)	II	0.4920	49.20%
Estrogen receptor binding	+	0.5337	53.37%
Androgen receptor binding	-	0.5252	52.52%
Thyroid receptor binding	-	0.5442	54.42%
Glucocorticoid receptor binding	+	0.6521	65.21%
Aromatase binding	-	0.5203	52.03%
PPAR gamma	-	0.6523	65.23%
Honey bee toxicity	-	0.9033	90.33%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.7761	77.61%

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