Lasiocarpine

Details

• Internal ID: ddf727c9-0eec-415f-bc13-478e67ee307e
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(7S,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCN2C1C(=CC2)COC(=O)C(C(C)OC)(C(C)(C)O)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)OC)(C(C)(C)O)O
• InChI: InChI=1S/C21H33NO7/c1-7-13(2)18(23)29-16-9-11-22-10-8-15(17(16)22)12-28-19(24)21(26,14(3)27-6)20(4,5)25/h7-8,14,16-17,25-26H,9-12H2,1-6H3/b13-7-/t14-,16-,17+,21-/m0/s1
• InChI Key: QHOZSLCIKHUPSU-LPLKQDONSA-N
• Popularity: 52 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₃NO₇
• Molecular Weight: 411.50 g/mol
• Exact Mass: 411.22570239 g/mol
• Topological Polar Surface Area (TPSA): 106.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.96
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

• 7-Angelyleuropine
• (-)-Lasiocarpine
• Europine 7-angelate
• 303-34-4
• NCI-C01478
• RCRA waste number U143
• CCRIS 355
• HSDB 6062
• UNII-S770100Q96
• NSC 30625
• NSC-30625
• AI3-51770
• S770100Q96
• Heliotridine ester with lasiocarpum and angelic acid
• LASIOCARPINE (IARC)
• LASIOCARPINE [IARC]
• (Z)-2-Methylcrotonic acid, 2,3-dihydroxy-2-(1-methoxyethyl)-3-methylbutyrate (ester)
• (7alpha-Angelyloxy-5,6,7,8alpha-tetrahydro-3H-pyrrolizin-1-yl)methyl-2,3-dihydroxy-2-(1'-methoxyethyl)-3-methylbutyrate
• 2,3,5,7alphabeta-Tetrahydro-1-hydroxy-1H-pyrrolizine-7-methanol-1-angelate-7-(2,3-dihydroxy-2(1-methoxyethyl))-3-methyl-butyrate
• 2-Butenoic acid, 2-methyl-, 7-((2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester, (1S-(1alpha(Z),7(2S*,3R*),7aalpha))-
• 2-Butenoic acid, 2-methy-,(1S,7aR)-7-(((2R)-2,3-dihydroxy-2-((1S)-1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-ester, (2Z)-
• 2-Butenoic acid, 2-methyl-, 7-((2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester, (1S-(1alpha(Z),7(2S*,3R*),7a alpha))-
• MLS002639334
• DTXSID1020772
• 7-Angelyl-9-lasiocarpylheliotridine
• NSC30625
• Heliotridine ester with lasiocarpum & angelic acid
• LASIOCARPINE [MI]
• RCRA waste no. U143
• LASIOCARPINE [HSDB]
• DTXCID70772
• SCHEMBL168932
• HELIOSUPINE METHYL ETHER
• CHEMBL1999554
• Lasiocarpine (7-Angelyleuropine)
• 2-methyl-2-butenoic acid 7-((2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester
• HELIOSUPINE METHYL ETHER [MI]
• Lasiocarpine 100 microg/mL in Water
• AKOS030501885
• 1ST14169
• WLN: T55 AN CUTJ D1OVXQXQ1 & 1 & Y1 & O1 FOVY1 & U2
• (1S,7aR)-7-((((R)-2,3-dihydroxy-2-((S)-1-methoxyethyl)-3-methylbutanoyl)oxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (Z)-2-methylbut-2-enoate
• (7-ALPHA-ANGELYLOXY-5,6,7,8-ALPHA-TETRAHYDRO-3H-PYRROLIZIN-1-YL)METHYL-2,3-DIHYDROXY-2-(1'-METHOXYETHYL)-3-METHYLBUTYRATE
• (Z)-2-METHYL-CROTONIC ACID, 2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYLBUTYRATE (ESTER)
• (Z)-2-METHYLCROTONIC ACID-2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYLBUTYRATE (ESTER)
• 2,3,5,7ALPHA, BETA-TETRAHYDRO-1-HYDROXYL-1H-PYRROLIZINE-7-METHANOL-1-ANGELATE-7-(2,3-DIHYDROXY)-2(1-METHOXYETHYL)-3-METHYLBUTYRATE
• 2-BUTENOIC ACID, 2-METHYL-, 7-((2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYL-1-OXOBUTOXY)METHYL)--2,3,5,7A-TETRAHYDRO-1H-PYRROLIZIN-1-YL ESTER, (1S-(1ALPHA(Z),7(2S*,3R*),7AALPHA))-
• 2-BUTENOIC ACID, 2-METHYL-, 7-((2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYL-1-OXOBUTOXY)METHYL)-2,3,5,7A-TETRAHYDRO-1H-PYRROLIZIN-1-YL ESTER, (1S-(1.ALPHA.(Z),7(S*(R*)),7A.ALPHA.))-
• 2-BUTENOIC ACID, 2-METHYL-, 7-((2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYL-1-OXOBUTOXY)METHYL)-2,3,5,7A-TETRAHYDRO-1H-PYRROLIZIN-1-YL ESTER, (1S-(1alpha(Z),7(S*(R*)),7Aalpha))-
• 2-Butenoic acid, 7-[[2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy]methyl]-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester, [1S-[1.alpha.(Z),7(2S*,3R*),7a.alpha.]]-
• 2-BUTENOIC ACID-2-METHYL-7((2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYL-1-OXOBUTOXY)METHYL)-2,3,5,7A-TETRAHYDRO-1H-PYRROLIZIN-1-YL-ESTER(1S-1-ALPHA (Z),-7(2S,3R)7-A-ALPHA))
• stereoisomer of 7-(2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy)-methyl-2,3,5,7alpha-tetrahydro-1H-pyrrolizin-1-yl-2-methyl-2-butenoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6134	61.34%
Caco-2	-	0.5403	54.03%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7876	78.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8854	88.54%
OATP1B3 inhibitior	+	0.9381	93.81%
MATE1 inhibitior	-	0.8809	88.09%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8733	87.33%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	+	0.5752	57.52%
CYP3A4 substrate	+	0.6381	63.81%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.7884	78.84%
CYP3A4 inhibition	-	0.9701	97.01%
CYP2C9 inhibition	-	0.8936	89.36%
CYP2C19 inhibition	-	0.8858	88.58%
CYP2D6 inhibition	-	0.7569	75.69%
CYP1A2 inhibition	-	0.8826	88.26%
CYP2C8 inhibition	-	0.6564	65.64%
CYP inhibitory promiscuity	-	0.9721	97.21%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Danger	0.7589	75.89%
Eye corrosion	-	0.9799	97.99%
Eye irritation	-	0.9746	97.46%
Skin irritation	-	0.7558	75.58%
Skin corrosion	-	0.9189	91.89%
Ames mutagenesis	+	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4413	44.13%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	1.0000	100.00%
skin sensitisation	-	0.8199	81.99%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6968	69.68%
Acute Oral Toxicity (c)	II	0.7224	72.24%
Estrogen receptor binding	+	0.5724	57.24%
Androgen receptor binding	+	0.5917	59.17%
Thyroid receptor binding	+	0.6304	63.04%
Glucocorticoid receptor binding	+	0.7308	73.08%
Aromatase binding	+	0.6179	61.79%
PPAR gamma	-	0.6000	60.00%
Honey bee toxicity	-	0.7491	74.91%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	-	0.6158	61.58%

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	98.85%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.99%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.08%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.71%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.21%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.44%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.65%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.62%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.23%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.21%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.56%	93.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.53%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.40%	91.19%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.39%	89.62%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.11%	90.24%

Plants that contains it

• Cynoglossum officinale

Cross-Links

• PubChem: 5281735
• LOTUS: LTS0029457
• wikiData: Q105221065