NP-MRD: Showing NP-Card for 3R-(3R-Hydroxybutyryloxy)butyric acid (NP0005029)

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Record Information

Version

1.0

Created at

2020-12-09 02:23:32 UTC

Updated at

2021-07-15 16:50:51 UTC

NP-MRD ID

NP0005029

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3R-(3R-Hydroxybutyryloxy)butyric acid

Provided By

NPAtlas

Description

(R)-3-[(R)-3-hydroxybutanoyloxy]butanoic acid is also known as 3R-(3R-hydroxybutyryloxy)butyric acid. 3R-(3R-Hydroxybutyryloxy)butyric acid is found in Annulohypoxylon truncatum, Apis cerana, Hypoxylon and Linyphia triangularis. It was first documented in 1993 (PMID: 17810206). Based on a literature review very few articles have been published on (R)-3-[(R)-3-hydroxybutanoyloxy]butanoic acid (PMID: 14695807).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118163D          

 27 26  0  0  0  0            999 V2000
    3.7432   -0.9510   -0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2877    0.4775   -0.1036 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0225    0.9204   -1.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1013    0.6661    0.7941 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9036   -0.0917    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8869   -1.3200    0.1629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128    0.5546    0.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4816   -0.0596   -0.1256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1064    0.3999   -1.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4942    0.0943    0.9766 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7493   -0.5707    0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8660   -1.8064    0.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8360    0.1967    0.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0096   -1.6031   -0.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7306   -1.0222   -0.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8682   -1.3767    0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1511    1.0820    0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075    0.1861   -1.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4019    0.3167    1.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8747    1.7407    0.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2863   -1.1484   -0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5589   -0.0463   -2.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2718    1.4754   -1.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1286   -0.0723   -1.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0911   -0.4006    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6799    1.1593    1.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7259    1.1992    0.0108 H   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  2 17  1  1  0  0  0
  3 18  1  0  0  0  0
  4 19  1  0  0  0  0
  4 20  1  0  0  0  0
  8 21  1  6  0  0  0
  9 22  1  0  0  0  0
  9 23  1  0  0  0  0
  9 24  1  0  0  0  0
 10 25  1  0  0  0  0
 10 26  1  0  0  0  0
 13 27  1  0  0  0  0
M  END


  Mrv1652306242118163D          

 27 26  0  0  0  0            999 V2000
    3.7432   -0.9510   -0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2877    0.4775   -0.1036 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0225    0.9204   -1.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1013    0.6661    0.7941 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9036   -0.0917    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8869   -1.3200    0.1629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128    0.5546    0.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4816   -0.0596   -0.1256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1064    0.3999   -1.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4942    0.0943    0.9766 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7493   -0.5707    0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8660   -1.8064    0.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8360    0.1967    0.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0096   -1.6031   -0.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7306   -1.0222   -0.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8682   -1.3767    0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1511    1.0820    0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075    0.1861   -1.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4019    0.3167    1.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8747    1.7407    0.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2863   -1.1484   -0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5589   -0.0463   -2.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2718    1.4754   -1.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1286   -0.0723   -1.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0911   -0.4006    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6799    1.1593    1.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7259    1.1992    0.0108 H   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  2 17  1  1  0  0  0
  3 18  1  0  0  0  0
  4 19  1  0  0  0  0
  4 20  1  0  0  0  0
  8 21  1  6  0  0  0
  9 22  1  0  0  0  0
  9 23  1  0  0  0  0
  9 24  1  0  0  0  0
 10 25  1  0  0  0  0
 10 26  1  0  0  0  0
 13 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005029

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@]([H])(OC(=O)C([H])([H])[C@]([H])(O[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O5/c1-5(9)3-8(12)13-6(2)4-7(10)11/h5-6,9H,3-4H2,1-2H3,(H,10,11)/t5-,6-/m1/s1

> <INCHI_KEY>
RILHUWWTCSDPAN-PHDIDXHHSA-N

> <FORMULA>
C8H14O5

> <MOLECULAR_WEIGHT>
190.195

> <EXACT_MASS>
190.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.617190737138593

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-3-{[(3R)-3-hydroxybutanoyl]oxy}butanoic acid

> <ALOGPS_LOGP>
0.06

> <JCHEM_LOGP>
-0.1095408740000001

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.407217281495427

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.225095081503412

> <JCHEM_PKA_STRONGEST_BASIC>
-2.620683437930942

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
43.43600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.15e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-{[(3R)-3-hydroxybutanoyl]oxy}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.743  -0.951  -0.184  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.288   0.478  -0.104  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.022   0.920  -1.411  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.101   0.666   0.794  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.904  -0.092   0.390  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.887  -1.320   0.163  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.313   0.555   0.237  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.482  -0.060  -0.126  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.106   0.400  -1.412  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.494   0.094   0.977  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.749  -0.571   0.582  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.866  -1.806   0.633  0.00  0.00           O+0
HETATM   13  O   UNK     0      -4.836   0.197   0.142  0.00  0.00           O+0
HETATM   14  H   UNK     0       3.010  -1.603  -0.720  0.00  0.00           H+0
HETATM   15  H   UNK     0       4.731  -1.022  -0.697  0.00  0.00           H+0
HETATM   16  H   UNK     0       3.868  -1.377   0.824  0.00  0.00           H+0
HETATM   17  H   UNK     0       4.151   1.082   0.241  0.00  0.00           H+0
HETATM   18  H   UNK     0       2.607   0.186  -1.952  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.402   0.317   1.833  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.875   1.741   0.933  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.286  -1.148  -0.256  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.559  -0.046  -2.261  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.272   1.475  -1.504  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.129  -0.072  -1.445  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.091  -0.401   1.887  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.680   1.159   1.213  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.726   1.199   0.011  0.00  0.00           H+0
CONECT    1    2   14   15   16                                             
CONECT    2    1    3    4   17                                             
CONECT    3    2   18                                                       
CONECT    4    2    5   19   20                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   21                                             
CONECT    9    8   22   23   24                                             
CONECT   10    8   11   25   26                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   27                                                       
CONECT   14    1                                                            
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    2                                                            
CONECT   18    3                                                            
CONECT   19    4                                                            
CONECT   20    4                                                            
CONECT   21    8                                                            
CONECT   22    9                                                            
CONECT   23    9                                                            
CONECT   24    9                                                            
CONECT   25   10                                                            
CONECT   26   10                                                            
CONECT   27   13                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(R)-3-[(R)-3-Hydroxybutanoyloxy]butanoate	Generator
3R-(3R-Hydroxybutyryloxy)butyric acid	MeSH

Chemical Formula

C₈H₁₄O₅

Average Mass

190.1950 Da

Monoisotopic Mass

190.08412 Da

IUPAC Name

(3R)-3-{[(3R)-3-hydroxybutanoyl]oxy}butanoic acid

Traditional Name

(3R)-3-{[(3R)-3-hydroxybutanoyl]oxy}butanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](O)CC(=O)O[C@H](C)CC(O)=O

InChI Identifier

InChI=1S/C8H14O5/c1-5(9)3-8(12)13-6(2)4-7(10)11/h5-6,9H,3-4H2,1-2H3,(H,10,11)/t5-,6-/m1/s1

InChI Key

RILHUWWTCSDPAN-PHDIDXHHSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Annulohypoxylon truncatum	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Hypoxylon	NPAtlas	14695807
Linyphia triangularis	-	KNApSAcK

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxylic ester (CHEBI:17663 )

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	0.06	ALOGPS
logP	-0.11	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	4.23	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	43.44 m³·mol⁻¹	ChemAxon
Polarizability	18.62 Å³	ChemAxon
Number of Rings	0	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

NPAtlas ID

NPA008678

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4573681

KEGG Compound ID

C04546

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5459971

PDB ID

Not Available

ChEBI ID

17663

Good Scents ID

Not Available

References

General References

Quang DN, Hashimoto T, Toyota M, Asakawa Y: Occurrence of a high concentration of spider pheromones in the ascomycete fungus Hypoxylon truncatum. J Nat Prod. 2003 Dec;66(12):1613-4. doi: 10.1021/np030185y. [PubMed:14695807 ]
Schulz S, Toft S: Identification of a sex pheromone from a spider. Science. 1993 Jun 11;260(5114):1635-7. doi: 10.1126/science.260.5114.1635. [PubMed:17810206 ]

Showing NP-Card for 3R-(3R-Hydroxybutyryloxy)butyric acid (NP0005029)

MOL for NP0005029 (3R-(3R-Hydroxybutyryloxy)butyric acid)

3D MOL for NP0005029 (3R-(3R-Hydroxybutyryloxy)butyric acid)

3D SDF for NP0005029 (3R-(3R-Hydroxybutyryloxy)butyric acid)

3D-SDF for NP0005029 (3R-(3R-Hydroxybutyryloxy)butyric acid)

PDB for NP0005029 (3R-(3R-Hydroxybutyryloxy)butyric acid)

3D PDB for NP0005029 (3R-(3R-Hydroxybutyryloxy)butyric acid)

SMILES for NP0005029 (3R-(3R-Hydroxybutyryloxy)butyric acid)

INCHI for NP0005029 (3R-(3R-Hydroxybutyryloxy)butyric acid)

Structure for NP0005029 (3R-(3R-Hydroxybutyryloxy)butyric acid)

3D Structure for NP0005029 (3R-(3R-Hydroxybutyryloxy)butyric acid)