NP-MRD: Showing NP-Card for (1s,2r,3r,7s,7ar)-3-(hydroxymethyl)-hexahydro-1h-pyrrolizine-1,2,7-triol (NP0320147)

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Record Information

Version

2.0

Created at

2022-09-11 21:38:18 UTC

Updated at

2022-09-11 21:38:18 UTC

NP-MRD ID

NP0320147

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,7s,7ar)-3-(hydroxymethyl)-hexahydro-1h-pyrrolizine-1,2,7-triol

Description

2-Ketobutyric acid, also known as 2-ketobutyrate, 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. 2-Ketobutyric acid is a very strong basic compound (based on its pKa). 2-Ketobutyric acid may be a unique E. Coli metabolite. Within humans, 2-ketobutyric acid participates in a number of enzymatic reactions. In particular, 2-ketobutyric acid can be biosynthesized from L-threonine through the action of the enzyme L-serine dehydratase/l-threonine deaminase. In addition, 2-ketobutyric acid and coenzyme A can be converted into propionyl-CoA; which is catalyzed by the enzyme branched-chain alpha-keto dehydrogenase complex. In humans, 2-ketobutyric acid is involved in threonine and 2-oxobutanoate degradation. Outside of the human body, 2-ketobutyric acid has been detected, but not quantified in, fruits. (1s,2r,3r,7s,7ar)-3-(hydroxymethyl)-hexahydro-1h-pyrrolizine-1,2,7-triol is found in Castanospermum australe. This could make 2-ketobutyric acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
    2.1808   -2.3564   -0.2476 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3753   -1.1130    0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2315   -0.2252   -0.0676 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3387    1.1608    0.5338 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2743    1.9537   -0.0664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0972    1.6377    0.2681 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2438    1.7034   -1.1018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8387    0.4057    0.7868 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2083    0.2764    0.2142 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4041    1.0303   -0.9376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2262   -1.1951   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7984   -1.3245   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -0.7023    0.3328 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5437   -2.8758    0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3914   -1.2084    1.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3094   -0.6230   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2430   -0.0935   -1.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4307    1.1021    1.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9939    2.2403    0.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3414    2.5426    0.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978    1.9019   -1.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8317    0.5047    1.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0269    0.4196    0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3758    1.1577   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2968   -1.8596    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9808   -1.3958   -0.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6952   -0.6958   -1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4933   -2.3682   -0.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
 13  8  1  0
  6  8  1  0
  8 22  1  1
  9 23  1  1
 10 24  1  0
 11 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
  3 17  1  6
  2 15  1  0
  2 16  1  0
  1 14  1  0
  4 18  1  1
  5 19  1  0
  6 20  1  1
  7 21  1  0
M  END


  Mrv1652309272007292D          

 14 15  0  0  0  0            999 V2000
   -4.7178   -0.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2328   -1.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2328   -0.1786    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1786   -0.8460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6636   -0.1786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4482   -0.4335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4482   -1.2585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6636   -1.5134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4482    0.3914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4087   -2.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4876    0.6059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4087    0.6059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3536   -0.8460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6016   -2.4695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  3  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  7  1  0  0  0  0
  8 10  1  1  0  0  0
  6  9  1  1  0  0  0
  3 11  1  6  0  0  0
  5 12  1  6  0  0  0
  4 13  1  6  0  0  0
 10 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320147

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12[C@@H](O)CCN1[C@H](CO)[C@@H](O)[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO4/c10-3-4-7(12)8(13)6-5(11)1-2-9(4)6/h4-8,10-13H,1-3H2/t4-,5+,6-,7-,8+/m1/s1

> <INCHI_KEY>
AIQMLBKBQCVDEY-UOLFYFMNSA-N

> <FORMULA>
C8H15NO4

> <MOLECULAR_WEIGHT>
189.211

> <EXACT_MASS>
189.100107967

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
18.88027631404276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,7S,7aR)-3-(hydroxymethyl)-hexahydro-1H-pyrrolizine-1,2,7-triol

> <ALOGPS_LOGP>
-2.05

> <JCHEM_LOGP>
-2.55449338

> <ALOGPS_LOGS>
0.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.213749252474837

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.152193183078392

> <JCHEM_PKA_STRONGEST_BASIC>
8.727070358260379

> <JCHEM_POLAR_SURFACE_AREA>
84.16000000000001

> <JCHEM_REFRACTIVITY>
44.4357

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,7S,7aR)-3-(hydroxymethyl)-hexahydro-1H-pyrrolizine-1,2,7-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -8.807  -1.579   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.901  -2.825   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.901  -0.333   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.067  -1.579   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.972  -0.333   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.437  -0.809   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -6.437  -2.349   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -4.972  -2.825   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      -6.437   0.731   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0      -4.496  -4.290   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -8.377   1.131   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.496   1.131   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.527  -1.579   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.990  -4.610   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    7                                                       
CONECT    3    1    6   11                                                  
CONECT    4    5    8   13                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    3    7    9                                             
CONECT    7    6    8    2                                                  
CONECT    8    4    7   10                                                  
CONECT    9    6                                                            
CONECT   10    8   14                                                       
CONECT   11    3                                                            
CONECT   12    5                                                            
CONECT   13    4                                                            
CONECT   14   10                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
2-Ketobutyrate	Generator
(1S,2R,3R,7S,7aR)-Hexahydro-3-(hydroxymethyl)-1H-pyrrolizine-1,2,7-triol	PhytoBank
(+)-1,7a-Diepialexine	PhytoBank
(+)-1-Epiaustraline	PhytoBank
(+)-1-epi-Australine	PhytoBank
1,7a-Diepialexine	PhytoBank
1-Epiaustraline	PhytoBank

Chemical Formula

C₈H₁₅NO₄

Average Mass

189.2110 Da

Monoisotopic Mass

189.10011 Da

IUPAC Name

(1S,2R,3R,7S,7aR)-3-(hydroxymethyl)-hexahydro-1H-pyrrolizine-1,2,7-triol

Traditional Name

(1S,2R,3R,7S,7aR)-3-(hydroxymethyl)-hexahydro-1H-pyrrolizine-1,2,7-triol

CAS Registry Number

Not Available

SMILES

[H][C@]12[C@@H](O)CCN1[C@H](CO)[C@@H](O)[C@H]2O

InChI Identifier

InChI=1S/C8H15NO4/c10-3-4-7(12)8(13)6-5(11)1-2-9(4)6/h4-8,10-13H,1-3H2/t4-,5+,6-,7-,8+/m1/s1

InChI Key

AIQMLBKBQCVDEY-UOLFYFMNSA-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

Species Name	Source	Reference
Castanospermum australe	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
N-alkylpyrrolidine
Pyrrolidine
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
1,2-aminoalcohol
Polyol
Azacycle
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
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	-2	ALOGPS
logP	-2.6	ChemAxon
logS	0.79	ALOGPS
pKa (Strongest Acidic)	13.15	ChemAxon
pKa (Strongest Basic)	8.73	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	84.16 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	44.44 m³·mol⁻¹	ChemAxon
Polarizability	18.88 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

FDB000001

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

453575

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,7s,7ar)-3-(hydroxymethyl)-hexahydro-1h-pyrrolizine-1,2,7-triol (NP0320147)

MOL for NP0320147 ((1s,2r,3r,7s,7ar)-3-(hydroxymethyl)-hexahydro-1h-pyrrolizine-1,2,7-triol)

3D MOL for NP0320147 ((1s,2r,3r,7s,7ar)-3-(hydroxymethyl)-hexahydro-1h-pyrrolizine-1,2,7-triol)

3D SDF for NP0320147 ((1s,2r,3r,7s,7ar)-3-(hydroxymethyl)-hexahydro-1h-pyrrolizine-1,2,7-triol)

3D-SDF for NP0320147 ((1s,2r,3r,7s,7ar)-3-(hydroxymethyl)-hexahydro-1h-pyrrolizine-1,2,7-triol)

PDB for NP0320147 ((1s,2r,3r,7s,7ar)-3-(hydroxymethyl)-hexahydro-1h-pyrrolizine-1,2,7-triol)

3D PDB for NP0320147 ((1s,2r,3r,7s,7ar)-3-(hydroxymethyl)-hexahydro-1h-pyrrolizine-1,2,7-triol)

SMILES for NP0320147 ((1s,2r,3r,7s,7ar)-3-(hydroxymethyl)-hexahydro-1h-pyrrolizine-1,2,7-triol)

INCHI for NP0320147 ((1s,2r,3r,7s,7ar)-3-(hydroxymethyl)-hexahydro-1h-pyrrolizine-1,2,7-triol)

Structure for NP0320147 ((1s,2r,3r,7s,7ar)-3-(hydroxymethyl)-hexahydro-1h-pyrrolizine-1,2,7-triol)

3D Structure for NP0320147 ((1s,2r,3r,7s,7ar)-3-(hydroxymethyl)-hexahydro-1h-pyrrolizine-1,2,7-triol)