NP-MRD: Showing NP-Card for 4-[(3s,5r)-5-[(1s)-1-hydroxypropyl]oxolan-3-yl]butanoic acid (NP0252840)

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Record Information

Version

2.0

Created at

2022-09-07 16:29:49 UTC

Updated at

2022-09-07 16:29:49 UTC

NP-MRD ID

NP0252840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(3s,5r)-5-[(1s)-1-hydroxypropyl]oxolan-3-yl]butanoic acid

Description

(5R,7S,8S)-Communiol A belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain. 4-[(3s,5r)-5-[(1s)-1-hydroxypropyl]oxolan-3-yl]butanoic acid is found in Podospora communis. Based on a literature review very few articles have been published on (5R,7S,8S)-Communiol A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
   -5.1278   -0.1381   -0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6994   -0.6069   -0.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9564   -0.1641    0.7245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0025    1.2108    0.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5402   -0.6701    0.7109 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8046   -0.0553   -0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4044    0.5370    0.1860 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6952    0.1738   -0.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8153    0.8352    0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1742    0.6068   -0.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5576   -0.8179   -0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8536   -1.7618   -0.0283 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8095   -1.1203   -0.9458 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4492   -0.1068    1.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8915   -0.2730    1.8675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8265   -0.9553   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3508    0.3050    0.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3235    0.6530   -1.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1784   -0.1465   -1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7037   -1.7131   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4775   -0.6019    1.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2161    1.6281    1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5119   -1.7628    0.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5807   -0.8320   -1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3828    0.7547   -0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589    1.6451    0.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6143    0.5977   -1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7644   -0.9179   -0.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7779    0.4574    1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6042    1.9223    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8995    1.1143    0.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2830    1.0809   -1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5567   -0.4325   -1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0107   -1.0576    1.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9456    0.6118    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
  7 14  1  0
 14 15  1  0
 15  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  1
  4 22  1  0
  5 23  1  6
  6 24  1  0
  6 25  1  0
  7 26  1  1
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
M  END


  Mrv1652309072218292D          

 15 15  0  0  1  0            999 V2000
   -5.4417    1.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6213    1.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1363    1.9391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4719    2.6928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3159    1.8529    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7638    2.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0101    2.1304    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2957    2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5812    2.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333    2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477    2.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    2.5429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477    1.3054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0964    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9034    1.1384    0.0000 O   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  6  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 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
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252840

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](O)[C@H]1C[C@H](CCCC(O)=O)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C11H20O4/c1-2-9(12)10-6-8(7-15-10)4-3-5-11(13)14/h8-10,12H,2-7H2,1H3,(H,13,14)/t8-,9-,10+/m0/s1

> <INCHI_KEY>
KOGNSOVIFNEWCD-LPEHRKFASA-N

> <FORMULA>
C11H20O4

> <MOLECULAR_WEIGHT>
216.277

> <EXACT_MASS>
216.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
24.006455691079157

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(3S,5R)-5-[(1S)-1-hydroxypropyl]oxolan-3-yl]butanoic acid

> <JCHEM_LOGP>
1.2175464356666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.20953803628771

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.421779410497484

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1445480647790855

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
55.3988

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(3S,5R)-5-[(1S)-1-hydroxypropyl]oxolan-3-yl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.158   2.535   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.626   2.374   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.721   3.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -8.348   5.027   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -6.190   3.459   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.159   4.603   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.752   3.977   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.419   4.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.085   3.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.249   4.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.582   3.977   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.916   4.747   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.582   2.437   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.913   2.445   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.420   2.125   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    7   15                                                       
CONECT   15   14    5                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₂₀O₄

Average Mass

216.2770 Da

Monoisotopic Mass

216.13616 Da

IUPAC Name

4-[(3S,5R)-5-[(1S)-1-hydroxypropyl]oxolan-3-yl]butanoic acid

Traditional Name

4-[(3S,5R)-5-[(1S)-1-hydroxypropyl]oxolan-3-yl]butanoic acid

CAS Registry Number

Not Available

SMILES

CC[C@H](O)[C@H]1C[C@H](CCCC(O)=O)CO1

InChI Identifier

InChI=1S/C11H20O4/c1-2-9(12)10-6-8(7-15-10)4-3-5-11(13)14/h8-10,12H,2-7H2,1H3,(H,13,14)/t8-,9-,10+/m0/s1

InChI Key

KOGNSOVIFNEWCD-LPEHRKFASA-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
Podospora communis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Heterocyclic fatty acids

Alternative Parents

Substituents

Heterocyclic fatty acid
Hydroxy fatty acid
Short-chain hydroxy acid
Oxolane
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	1.22	ChemAxon
pKa (Strongest Acidic)	4.42	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	55.4 m³·mol⁻¹	ChemAxon
Polarizability	24.01 Å³	ChemAxon
Number of Rings	1	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

9790204

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11615455

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[(3s,5r)-5-[(1s)-1-hydroxypropyl]oxolan-3-yl]butanoic acid (NP0252840)

MOL for NP0252840 (4-[(3s,5r)-5-[(1s)-1-hydroxypropyl]oxolan-3-yl]butanoic acid)

3D MOL for NP0252840 (4-[(3s,5r)-5-[(1s)-1-hydroxypropyl]oxolan-3-yl]butanoic acid)

3D SDF for NP0252840 (4-[(3s,5r)-5-[(1s)-1-hydroxypropyl]oxolan-3-yl]butanoic acid)

3D-SDF for NP0252840 (4-[(3s,5r)-5-[(1s)-1-hydroxypropyl]oxolan-3-yl]butanoic acid)

PDB for NP0252840 (4-[(3s,5r)-5-[(1s)-1-hydroxypropyl]oxolan-3-yl]butanoic acid)

3D PDB for NP0252840 (4-[(3s,5r)-5-[(1s)-1-hydroxypropyl]oxolan-3-yl]butanoic acid)

SMILES for NP0252840 (4-[(3s,5r)-5-[(1s)-1-hydroxypropyl]oxolan-3-yl]butanoic acid)

INCHI for NP0252840 (4-[(3s,5r)-5-[(1s)-1-hydroxypropyl]oxolan-3-yl]butanoic acid)

Structure for NP0252840 (4-[(3s,5r)-5-[(1s)-1-hydroxypropyl]oxolan-3-yl]butanoic acid)

3D Structure for NP0252840 (4-[(3s,5r)-5-[(1s)-1-hydroxypropyl]oxolan-3-yl]butanoic acid)