Np mrd loader

Showing NP-Card for 1-ethyl 3-(7-hydroxy-hexahydro-1h-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate (NP0291144)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2022-09-09 22:07:36 UTC
Updated at2022-09-09 22:07:36 UTC
NP-MRD IDNP0291144
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-ethyl 3-(7-hydroxy-hexahydro-1h-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate
Description1-Ethyl 3-(7-hydroxy-hexahydro-1H-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. 1-ethyl 3-(7-hydroxy-hexahydro-1h-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate is found in Ligularia fischeri. It was first documented in 2022 (PMID: 36115695). Based on a literature review a significant number of articles have been published on 1-ethyl 3-(7-hydroxy-hexahydro-1H-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate (PMID: 36115691) (PMID: 36115694) (PMID: 36115693) (PMID: 36115692).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0291144 (1-ethyl 3-(7-hydroxy-hexahydro-1h-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate)


  Mrv1652309102200072D          

 22 23  0  0  0  0            999 V2000
   -3.5723   -1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653   -1.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2133   -2.3931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4063   -2.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1514   -1.4370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543   -2.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -3.2762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -1.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937   -1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1092   -3.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9162   -3.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5572   -4.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
 14 19  1  0  0  0  0
  6 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
Download

3D MOL for NP0291144 (1-ethyl 3-(7-hydroxy-hexahydro-1h-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate)

Download
3D SDF for NP0291144 (1-ethyl 3-(7-hydroxy-hexahydro-1h-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate)

  Mrv1652309102200072D          

 22 23  0  0  0  0            999 V2000
   -3.5723   -1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653   -1.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2133   -2.3931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4063   -2.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1514   -1.4370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543   -2.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -3.2762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -1.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937   -1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1092   -3.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9162   -3.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5572   -4.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
 14 19  1  0  0  0  0
  6 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291144

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)C(=C(C)C)C(=O)OCC1CCN2CCC(O)C12

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO5/c1-4-21-15(19)13(10(2)3)16(20)22-9-11-5-7-17-8-6-12(18)14(11)17/h11-12,14,18H,4-9H2,1-3H3

> <INCHI_KEY>
OQUWOILRYVFVRO-UHFFFAOYSA-N

> <FORMULA>
C16H25NO5

> <MOLECULAR_WEIGHT>
311.378

> <EXACT_MASS>
311.173272909

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
32.90767916067584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-ethyl 3-(7-hydroxy-hexahydro-1H-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate

> <JCHEM_LOGP>
1.2677112420000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.542327530858774

> <JCHEM_PKA_STRONGEST_BASIC>
9.69095237942068

> <JCHEM_POLAR_SURFACE_AREA>
76.07000000000001

> <JCHEM_REFRACTIVITY>
81.7064

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-ethyl 3-(7-hydroxy-hexahydro-1H-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0291144 (1-ethyl 3-(7-hydroxy-hexahydro-1h-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate)
Download
PDB for NP0291144 (1-ethyl 3-(7-hydroxy-hexahydro-1h-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate)
HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668  -3.643   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.162  -3.323   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.131  -4.467   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.625  -4.147   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.149  -2.682   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.595  -5.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.088  -4.971   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.942  -6.116   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.388  -3.507   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.894  -3.186   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.834   0.294   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.204  -0.476   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.775  -3.186   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.071  -6.756   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.577  -7.076   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.040  -7.900   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   20                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11   14                                                  
CONECT   20    6   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

Download
3D PDB for NP0291144 (1-ethyl 3-(7-hydroxy-hexahydro-1h-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate)
Download
SMILES for NP0291144 (1-ethyl 3-(7-hydroxy-hexahydro-1h-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate)
CCOC(=O)C(=C(C)C)C(=O)OCC1CCN2CCC(O)C12
Download
INCHI for NP0291144 (1-ethyl 3-(7-hydroxy-hexahydro-1h-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate)
InChI=1S/C16H25NO5/c1-4-21-15(19)13(10(2)3)16(20)22-9-11-5-7-17-8-6-12(18)14(11)17/h11-12,14,18H,4-9H2,1-3H3
Download
View in JSmol
Synonyms
ValueSource
1-Ethyl 3-(7-hydroxy-hexahydro-1H-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioic acidGenerator
Chemical FormulaC16H25NO5
Average Mass311.3780 Da
Monoisotopic Mass311.17327 Da
IUPAC Name1-ethyl 3-(7-hydroxy-hexahydro-1H-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate
Traditional Name1-ethyl 3-(7-hydroxy-hexahydro-1H-pyrrolizin-1-yl)methyl 2-(propan-2-ylidene)propanedioate
CAS Registry NumberNot Available
SMILES
CCOC(=O)C(=C(C)C)C(=O)OCC1CCN2CCC(O)C12
InChI Identifier
InChI=1S/C16H25NO5/c1-4-21-15(19)13(10(2)3)16(20)22-9-11-5-7-17-8-6-12(18)14(11)17/h11-12,14,18H,4-9H2,1-3H3
InChI KeyOQUWOILRYVFVRO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ligularia fischeriLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrrolizidines  
Sub ClassNot Available
Direct ParentPyrrolizidines  
Alternative Parents
Substituents
  • Pyrrolizidine
    • 

  • Fatty acid ester
    • 

  • Dicarboxylic acid or derivatives
    • 

  • N-alkylpyrrolidine
    • 

  • Fatty acyl
    • 

  • Pyrrolidine
    • 

  • Enoate ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Amino acid or derivatives
    • 

  • Tertiary aliphatic amine
    • 

  • Tertiary amine
    • 

  • Secondary alcohol
    • 

  • 1,2-aminoalcohol
    • 

  • Carboxylic acid ester
    • 

  • Azacycle
    • 

  • Carboxylic acid derivative
    • 

  • Alcohol
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organopnictogen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Amine
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.27ChemAxon
pKa (Strongest Acidic)14.54ChemAxon
pKa (Strongest Basic)9.69ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.07 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity81.71 m³·mol⁻¹ChemAxon
Polarizability32.91 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163105418  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Hosokawa K, Nakao S: Somatic mutations and clonal expansions in paroxysmal nocturnal hemoglobinuria. Semin Hematol. 2022 Jul;59(3):143-149. doi: 10.1053/j.seminhematol.2022.08.004. Epub 2022 Aug 22. [PubMed:36115691  ] 
  2. eBioMedicine: The dynamics of the immune system and gut in the pathophysiology of multiple sclerosis. EBioMedicine. 2022 Sep;83:104273. doi: 10.1016/j.ebiom.2022.104273. [PubMed:36115695  ] 
  3. Lundgren S, Keranen M, Wartiovaara-Kautto U, Myllymaki M: Somatic compensation of inherited bone marrow failure. Semin Hematol. 2022 Jul;59(3):167-173. doi: 10.1053/j.seminhematol.2022.07.002. Epub 2022 Aug 3. [PubMed:36115694  ] 
  4. Alcedo PE, Gutierrez-Rodrigues F, Patel BA: Somatic mutations in VEXAS Syndrome and Erdheim-Chester disease: Inflammatory myeloid diseases. Semin Hematol. 2022 Jul;59(3):156-166. doi: 10.1053/j.seminhematol.2022.07.003. Epub 2022 Aug 3. [PubMed:36115693  ] 
  5. Todisco G, Moura PL, Hellstrom-Lindberg E: Clinical manifestations of clonal hematopoiesis: What has SF3B1-mutant MDS taught us? Semin Hematol. 2022 Jul;59(3):150-155. doi: 10.1053/j.seminhematol.2022.08.002. Epub 2022 Aug 11. [PubMed:36115692  ] 
  6. LOTUS database [Link]