NP-MRD: Showing NP-Card for (1s,7ar)-7-({[(2s)-2,3-dihydroxy-2-[(1s)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2z)-2-methylbut-2-enoate (NP0326664)

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Record Information

Version

2.0

Created at

2022-09-12 08:27:00 UTC

Updated at

2022-09-12 08:27:00 UTC

NP-MRD ID

NP0326664

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,7ar)-7-({[(2s)-2,3-dihydroxy-2-[(1s)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2z)-2-methylbut-2-enoate

Description

Lasiocarpine belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. They may act as prolonged, potent inhibitors of mitosis in hepatocytes, they are mutagenic in Drosophila and cause chromosome breakage in leukocytes. Lasiocarpine is a very strong basic compound (based on its pKa). Lasiocarpine is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. The prominence of rough ER in enlarged hepatocytes is s a sign of increased metabolic activity. Lasiocarpine is toxic to liver cells but not to lung cells, which is unable to metabolize the pyrrolizidine alkaloids to pyrroles. One of the unusual results of chronic poisoning by lasiocarpine and other members of the pyrrolizidine alkaloids is progressive enlargement of liver cells to up to three times the normal diameter, with an accompanying proportionate increase in nuclear diameter. The application of lasiocarpine to human liver cells in culture is followed by inhibition of DNA, RNA and protein synthesis; vacuolation of the cells, the prevention of mitosis and the formation of giant cells (“megalocytes”). Effects on the liver include hemorrhagic necrosis of parenchymal cells, marked enlargement of parenchymal cells and of their nuclei and nucleoli, fibrosis or cirrhosis, depression of cell division, and possibly neoplasia. The inducibility of tryptophan pyrrolase activity by hydrocortisone, in the livers of rats treated chronically with lasiocarpine is an indication that translational mechanisms are intact. However, the increased uptake of 3H-thymidine by megalocytes, in the absence of observable mitotic activity, suggests that these cells are in the process of hypertrophy.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 08291401032D          

 33 34  0  0  1  0            999 V2000
    5.5146   -0.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6036   -1.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4660   -2.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8027   -3.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289   -2.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8091   -4.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9626   -1.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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 29 62  1  6
M  END


  Mrv0541 08291401032D          

 33 34  0  0  1  0            999 V2000
    5.5146   -0.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6036   -1.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4660   -2.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8027   -3.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4527    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0326664

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(C)=C(/C)C(=O)O[C@@]1([H])CCN2CC=C(COC(=O)[C@](O)([C@]([H])(C)OC)C(C)(C)O)[C@]12[H]

> <INCHI_IDENTIFIER>
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-PNFBIMPKSA-N

> <FORMULA>
C21H33NO7

> <MOLECULAR_WEIGHT>
411.4892

> <EXACT_MASS>
411.225702415

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.352033633038566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,7aR)-7-({[(2S)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
1.3276952496666659

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.54820733944122

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.538190127297977

> <JCHEM_PKA_STRONGEST_BASIC>
7.135899253754255

> <JCHEM_POLAR_SURFACE_AREA>
105.53000000000002

> <JCHEM_REFRACTIVITY>
108.12859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,7aR)-7-({[(2S)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0      10.294  -1.655   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.727  -3.624   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.870  -5.003   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.365  -6.623   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.654  -4.562   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.510  -8.015   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.264  -2.800   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.204   2.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.370   3.262   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.299   3.262   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.894  -0.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.757  -2.479   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.335  -5.479   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.834   1.246   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.281  -1.015   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.449  -3.304   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.509  -5.593   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.479  -4.448   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       3.834   2.786   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0       8.312   0.130   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.942  -3.624   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.540  -6.737   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.623  -3.418   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.655  -6.985   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.924  -1.839   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.775  -0.695   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0       9.739  -4.264   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.014  -3.972   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.210  -0.319   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.080   2.151   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   20                                                            
CONECT    5   20                                                            
CONECT    6   27                                                            
CONECT    7    1   13   30                                                  
CONECT    8   10   15                                                       
CONECT    9   11   16                                                       
CONECT   10    8   22                                                       
CONECT   11    9   22                                                       
CONECT   12   15   28                                                       
CONECT   13    2    7   18                                                  
CONECT   14    3   21   27   31                                             
CONECT   15    8   12   17                                                  
CONECT   16    9   17   29   32                                             
CONECT   17   15   16   22   33                                             
CONECT   18   13   23   29                                                  
CONECT   19   21   24   28                                                  
CONECT   20    4    5   21   25                                             
CONECT   21   14   19   20   26                                             
CONECT   22   10   11   17                                                  
CONECT   23   18                                                            
CONECT   24   19                                                            
CONECT   25   20                                                            
CONECT   26   21                                                            
CONECT   27    6   14                                                       
CONECT   28   12   19                                                       
CONECT   29   16   18                                                       
CONECT   30    7                                                            
CONECT   31   14                                                            
CONECT   32   16                                                            
CONECT   33   17                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Value	Source
Lasiocarpine sulfate, (1S-(1alpha(Z),7(2S,3R),7aalpha))-isomer	MeSH
Lasiocarpine hydrochloride, (1S-(1alpha(Z),7(2S,3R),7aalpha))-isomer	MeSH

Chemical Formula

C₂₁H₃₃NO₇

Average Mass

411.4892 Da

Monoisotopic Mass

411.22570 Da

IUPAC Name

(1S,7aR)-7-({[(2S)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(1S,7aR)-7-({[(2S)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H]\C(C)=C(/C)C(=O)O[C@@]1([H])CCN2CC=C(COC(=O)[C@](O)([C@]([H])(C)OC)C(C)(C)O)[C@]12[H]

InChI Identifier

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-PNFBIMPKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Alkaloid or derivatives
Pyrrolizine
Fatty acid ester
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrrolidine
Tertiary alcohol
Pyrroline
Amino acid or derivatives
Carboxylic acid ester
1,2-diol
Tertiary aliphatic amine
Tertiary amine
Azacycle
Carboxylic acid derivative
Dialkyl ether
Organoheterocyclic compound
Ether
Organopnictogen compound
Amine
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Alcohol
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.95	ALOGPS
logP	1.33	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	10.54	ChemAxon
pKa (Strongest Basic)	7.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.53 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	108.13 m³·mol⁻¹	ChemAxon
Polarizability	43.35 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6321388

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,7ar)-7-({[(2s)-2,3-dihydroxy-2-[(1s)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2z)-2-methylbut-2-enoate (NP0326664)

MOL for NP0326664 ((1s,7ar)-7-({[(2s)-2,3-dihydroxy-2-[(1s)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0326664 ((1s,7ar)-7-({[(2s)-2,3-dihydroxy-2-[(1s)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0326664 ((1s,7ar)-7-({[(2s)-2,3-dihydroxy-2-[(1s)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0326664 ((1s,7ar)-7-({[(2s)-2,3-dihydroxy-2-[(1s)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2z)-2-methylbut-2-enoate)

PDB for NP0326664 ((1s,7ar)-7-({[(2s)-2,3-dihydroxy-2-[(1s)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0326664 ((1s,7ar)-7-({[(2s)-2,3-dihydroxy-2-[(1s)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0326664 ((1s,7ar)-7-({[(2s)-2,3-dihydroxy-2-[(1s)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0326664 ((1s,7ar)-7-({[(2s)-2,3-dihydroxy-2-[(1s)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2z)-2-methylbut-2-enoate)

Structure for NP0326664 ((1s,7ar)-7-({[(2s)-2,3-dihydroxy-2-[(1s)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0326664 ((1s,7ar)-7-({[(2s)-2,3-dihydroxy-2-[(1s)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-yl (2z)-2-methylbut-2-enoate)