NP-MRD: Showing NP-Card for hexahydro-1h-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate (NP0156926)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 14:12:28 UTC

Updated at

2022-09-02 14:12:28 UTC

NP-MRD ID

NP0156926

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hexahydro-1h-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate

Description

(Hexahydro-1H-pyrrolizin-1-yl)methyl 2,3-dihydroxy-3-methylpentanoate belongs to the class of organic compounds known as pyrrolizidines. hexahydro-1h-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate is found in Heliotropium strigosum. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom (hexahydro-1H-pyrrolizin-1-yl)methyl 2,3-dihydroxy-3-methylpentanoate is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241512412D          

 19 20  0  0  0  0            999 V2000
   -2.1711   -4.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3642   -4.4039    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
   -0.3246   -3.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8938   -3.3644    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
   -1.4063   -2.2216    0.0000 O   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
    2.0542   -0.6674    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
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 15 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156926

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)(O)C(O)C(=O)OCC1CCN2CCCC12

> <INCHI_IDENTIFIER>
InChI=1S/C14H25NO4/c1-3-14(2,18)12(16)13(17)19-9-10-6-8-15-7-4-5-11(10)15/h10-12,16,18H,3-9H2,1-2H3

> <INCHI_KEY>
NQWNEWFDQVQZAT-UHFFFAOYSA-N

> <FORMULA>
C14H25NO4

> <MOLECULAR_WEIGHT>
271.357

> <EXACT_MASS>
271.178358289

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
29.980899428853668

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(hexahydro-1H-pyrrolizin-1-yl)methyl 2,3-dihydroxy-3-methylpentanoate

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
0.23716363469327748

> <ALOGPS_LOGS>
-0.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.620452100846165

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.622793989633243

> <JCHEM_PKA_STRONGEST_BASIC>
10.182202135906218

> <JCHEM_POLAR_SURFACE_AREA>
70.0

> <JCHEM_REFRACTIVITY>
71.51410000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.93e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexahydro-1H-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -4.053  -8.541   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.546  -8.221   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.071  -6.756   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.606  -7.232   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.535  -6.280   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  O   UNK     0      -2.625  -4.147   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.088  -4.971   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.942  -6.116   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.388  -3.507   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.894  -3.186   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       3.834   0.294   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.204  -0.476   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   12   15                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
(Hexahydro-1H-pyrrolizin-1-yl)methyl 2,3-dihydroxy-3-methylpentanoic acid	Generator

Chemical Formula

C₁₄H₂₅NO₄

Average Mass

271.3570 Da

Monoisotopic Mass

271.17836 Da

IUPAC Name

(hexahydro-1H-pyrrolizin-1-yl)methyl 2,3-dihydroxy-3-methylpentanoate

Traditional Name

hexahydro-1H-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate

CAS Registry Number

Not Available

SMILES

CCC(C)(O)C(O)C(=O)OCC1CCN2CCCC12

InChI Identifier

InChI=1S/C14H25NO4/c1-3-14(2,18)12(16)13(17)19-9-10-6-8-15-7-4-5-11(10)15/h10-12,16,18H,3-9H2,1-2H3

InChI Key

NQWNEWFDQVQZAT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Heliotropium strigosum	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizidines

Sub Class

Not Available

Direct Parent

Pyrrolizidines

Alternative Parents

Substituents

Pyrrolizidine
Fatty acid ester
Monosaccharide
N-alkylpyrrolidine
Fatty acyl
Pyrrolidine
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Secondary alcohol
1,2-diol
Carboxylic acid ester
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Alcohol
Amine
Hydrocarbon derivative
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	0.93	ALOGPS
logP	0.24	ChemAxon
logS	-0.84	ALOGPS
pKa (Strongest Acidic)	11.62	ChemAxon
pKa (Strongest Basic)	10.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	71.51 m³·mol⁻¹	ChemAxon
Polarizability	29.98 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

169554

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for hexahydro-1h-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate (NP0156926)

MOL for NP0156926 (hexahydro-1h-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate)

3D MOL for NP0156926 (hexahydro-1h-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate)

3D SDF for NP0156926 (hexahydro-1h-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate)

3D-SDF for NP0156926 (hexahydro-1h-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate)

PDB for NP0156926 (hexahydro-1h-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate)

3D PDB for NP0156926 (hexahydro-1h-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate)

SMILES for NP0156926 (hexahydro-1h-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate)

INCHI for NP0156926 (hexahydro-1h-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate)

Structure for NP0156926 (hexahydro-1h-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate)

3D Structure for NP0156926 (hexahydro-1h-pyrrolizin-1-ylmethyl 2,3-dihydroxy-3-methylpentanoate)