NP-MRD: Showing NP-Card for ascr#2 (NP0307471)

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Record Information

Version

2.0

Created at

2022-09-11 00:36:54 UTC

Updated at

2022-09-11 00:36:54 UTC

NP-MRD ID

NP0307471

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ascr#2

Description

Ascr#2, also known as ascaroside C6 or daumone-2, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Thus, ascr#2 is considered to be a fatty acyl glycoside. Ascr#2 is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. ascr#2 is found in Caenorhabditis elegans. ascr#2 was first documented in 2012 (PMID: 22701701). Based on a literature review a small amount of articles have been published on ascr#2 (PMID: 35094091) (PMID: 29480728) (PMID: 23509272) (PMID: 22665789).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    5.4387   -0.7149    1.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1361   -1.0934    1.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7479   -2.2298    1.2230 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3168   -0.1079    0.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0654   -0.7815   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1648    0.1936   -0.8796 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9336    0.7137   -2.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.5430   -1.2428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1193   -0.1153   -0.6536 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6965   -1.0432    0.1760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0037   -0.6481    0.4605 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5239   -1.3022    1.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1319    0.8584    0.5263 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3866    1.1744    1.0462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0520    1.3581   -0.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1121    0.4152   -1.6572 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4526    1.2076   -2.6094 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3310   -0.0670    2.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0171   -0.1623    0.9329 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0291   -1.6129    1.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9758    0.7071    1.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625    0.4178   -0.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4372   -1.1488    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2771   -1.6105   -0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9266    1.0143   -0.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2240    1.7645   -1.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839    0.1602   -2.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3326    0.6157   -3.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8260    0.7633   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6424   -0.9916   -0.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9725   -2.2997    1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3086   -0.6774    2.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6773   -1.4746    2.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3865    1.3308    1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0907    0.5577    0.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0843    1.2030   -1.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7292    2.3974   -0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6439   -0.3650   -2.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3174    2.1362   -2.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16  9  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  6 25  1  1
  5 23  1  0
  5 24  1  0
  4 21  1  0
  4 22  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  9 29  1  1
 11 30  1  6
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  1
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  6
 17 39  1  0
M  END


  Mrv1652309112202372D          

 17 17  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0307471

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC(C)=O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H22O5/c1-7(13)4-5-8(2)16-12-11(15)6-10(14)9(3)17-12/h8-12,14-15H,4-6H2,1-3H3/t8-,9+,10-,11-,12-/m1/s1

> <INCHI_KEY>
KDIFLHQRDPSWHT-IYKVGLELSA-N

> <FORMULA>
C12H22O5

> <MOLECULAR_WEIGHT>
246.303

> <EXACT_MASS>
246.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.14352530660542

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-5-{[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxy}hexan-2-one

> <JCHEM_LOGP>
0.19764973033333383

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.278529391888732

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.264072270887514

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1878253685559272

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
61.5427

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-5-{[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxy}hexan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
(-)-5R-(3'r,5'r-Dihydroxy-6's-methyl-(2H)-tetrahydropyran-2'-yloxy)-2-hexanone	ChEBI
Ascaroside C6	ChEBI
Daumone-2	ChEBI

Chemical Formula

C₁₂H₂₂O₅

Average Mass

246.3030 Da

Monoisotopic Mass

246.14672 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H](CCC(C)=O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O

InChI Identifier

InChI=1S/C12H22O5/c1-7(13)4-5-8(2)16-12-11(15)6-10(14)9(3)17-12/h8-12,14-15H,4-6H2,1-3H3/t8-,9+,10-,11-,12-/m1/s1

InChI Key

KDIFLHQRDPSWHT-IYKVGLELSA-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
Caenorhabditis elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Oxane
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Acetal
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

methyl ketone (CHEBI:78812 )
hydroxy ketone ascaroside (CHEBI:78812 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00045627

Chemspider ID

17226058

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16066475

PDB ID

Not Available

ChEBI ID

78812

Good Scents ID

Not Available

References

General References

Cohen SM, Wrobel CJJ, Prakash SJ, Schroeder FC, Sternberg PW: Formation and function of dauer ascarosides in the nematodes Caenorhabditis briggsae and Caenorhabditis elegans. G3 (Bethesda). 2022 Mar 4;12(3):jkac014. doi: 10.1093/g3journal/jkac014. [PubMed:35094091 ]
Dong C, Reilly DK, Bergame C, Dolke F, Srinivasan J, von Reuss SH: Comparative Ascaroside Profiling of Caenorhabditis Exometabolomes Reveals Species-Specific (omega) and (omega - 2)-Hydroxylation Downstream of Peroxisomal beta-Oxidation. J Org Chem. 2018 Jul 6;83(13):7109-7120. doi: 10.1021/acs.joc.8b00094. Epub 2018 Mar 5. [PubMed:29480728 ]
Ludewig AH, Izrayelit Y, Park D, Malik RU, Zimmermann A, Mahanti P, Fox BW, Bethke A, Doering F, Riddle DL, Schroeder FC: Pheromone sensing regulates Caenorhabditis elegans lifespan and stress resistance via the deacetylase SIR-2.1. Proc Natl Acad Sci U S A. 2013 Apr 2;110(14):5522-7. doi: 10.1073/pnas.1214467110. Epub 2013 Mar 18. [PubMed:23509272 ]
Kaplan F, Alborn HT, von Reuss SH, Ajredini R, Ali JG, Akyazi F, Stelinski LL, Edison AS, Schroeder FC, Teal PE: Interspecific nematode signals regulate dispersal behavior. PLoS One. 2012;7(6):e38735. doi: 10.1371/journal.pone.0038735. Epub 2012 Jun 6. [PubMed:22701701 ]
Park D, O'Doherty I, Somvanshi RK, Bethke A, Schroeder FC, Kumar U, Riddle DL: Interaction of structure-specific and promiscuous G-protein-coupled receptors mediates small-molecule signaling in Caenorhabditis elegans. Proc Natl Acad Sci U S A. 2012 Jun 19;109(25):9917-22. doi: 10.1073/pnas.1202216109. Epub 2012 Jun 4. [PubMed:22665789 ]
LOTUS database [Link]

Showing NP-Card for ascr#2 (NP0307471)

MOL for NP0307471 (ascr#2)

3D MOL for NP0307471 (ascr#2)

3D SDF for NP0307471 (ascr#2)

3D-SDF for NP0307471 (ascr#2)

PDB for NP0307471 (ascr#2)

3D PDB for NP0307471 (ascr#2)

SMILES for NP0307471 (ascr#2)

INCHI for NP0307471 (ascr#2)

Structure for NP0307471 (ascr#2)

3D Structure for NP0307471 (ascr#2)