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Showing NP-Card for Diatretyne 2 (NP0004881)

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Record Information
Version2.0
Created at2020-12-09 02:17:13 UTC
Updated at2021-08-19 23:59:36 UTC
NP-MRD IDNP0004881
Secondary Accession NumbersNone
Natural Product Identification
Common NameDiatretyne 2
Provided ByNPAtlasNPAtlas Logo
DescriptionDiatretin 2, also known as diatretyne II or nudic acid b, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Diatretyne 2 is found in Camarophyllus virgineus and Clitocybe. Diatretyne 2 was first documented in 1955 (PMID: 14372966). Based on a literature review very few articles have been published on Diatretin 2.
Structure
Data?1624574223
MOL3D MOLSDF3D SDFPDBSMILESInChI

MOL for NP0004881 (Diatretyne 2)


  Mrv1652306242118093D          

 14 13  0  0  0  0            999 V2000
   -6.6665   -0.6914   -0.3830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5131   -0.5383   -0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1084   -0.3418   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9088   -0.1763   -0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5080    0.0345   -0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129    0.2330    0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0941    0.4877    0.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9488   -0.4897   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738   -0.2397    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2372   -1.1428   -0.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    1.0059    0.4865 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5022    1.4463    0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5756   -1.4718   -0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4671    1.8843    0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  3  0  0  0  0
  4  5  1  0  0  0  0
  5  6  3  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
M  END
Download

3D MOL for NP0004881 (Diatretyne 2)

     RDKit          3D

 14 13  0  0  0  0  0  0  0  0999 V2000
   -6.6665   -0.6914   -0.3830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5131   -0.5383   -0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1084   -0.3418   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9088   -0.1763   -0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5080    0.0345   -0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129    0.2330    0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0941    0.4877    0.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9488   -0.4897   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738   -0.2397    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2372   -1.1428   -0.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    1.0059    0.4865 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5022    1.4463    0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5756   -1.4718   -0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4671    1.8843    0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  3  0
  4  5  1  0
  5  6  3  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
  8 13  1  0
 11 14  1  0
M  END
Download

3D SDF for NP0004881 (Diatretyne 2)


  Mrv1652306242118093D          

 14 13  0  0  0  0            999 V2000
   -6.6665   -0.6914   -0.3830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5131   -0.5383   -0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1084   -0.3418   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9088   -0.1763   -0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5080    0.0345   -0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129    0.2330    0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0941    0.4877    0.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9488   -0.4897   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738   -0.2397    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2372   -1.1428   -0.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    1.0059    0.4865 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5022    1.4463    0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5756   -1.4718   -0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4671    1.8843    0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  3  0  0  0  0
  4  5  1  0  0  0  0
  5  6  3  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004881

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\[H])=C(/[H])C#CC#CC#N

> <INCHI_IDENTIFIER>
InChI=1S/C8H3NO2/c9-7-5-3-1-2-4-6-8(10)11/h4,6H,(H,10,11)/b6-4+

> <INCHI_KEY>
DMGKNZBGIHCAMP-GQCTYLIASA-N

> <FORMULA>
C8H3NO2

> <MOLECULAR_WEIGHT>
145.1149

> <EXACT_MASS>
145.016378345

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
14.174642546320756

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-7-cyanohept-2-en-4,6-diynoic acid

> <ALOGPS_LOGP>
1.32

> <JCHEM_LOGP>
1.2835784089999998

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.196448962120338

> <JCHEM_POLAR_SURFACE_AREA>
61.09

> <JCHEM_REFRACTIVITY>
40.7882

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-7-cyanohept-2-en-4,6-diynoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0004881 (Diatretyne 2)

     RDKit          3D

 14 13  0  0  0  0  0  0  0  0999 V2000
   -6.6665   -0.6914   -0.3830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5131   -0.5383   -0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1084   -0.3418   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9088   -0.1763   -0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5080    0.0345   -0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129    0.2330    0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0941    0.4877    0.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9488   -0.4897   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738   -0.2397    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2372   -1.1428   -0.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    1.0059    0.4865 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5022    1.4463    0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5756   -1.4718   -0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4671    1.8843    0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  3  0
  4  5  1  0
  5  6  3  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
  8 13  1  0
 11 14  1  0
M  END
Download

PDB for NP0004881 (Diatretyne 2)

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  N   UNK     0      -6.667  -0.691  -0.383  0.00  0.00           N+0
HETATM    2  C   UNK     0      -5.513  -0.538  -0.324  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.108  -0.342  -0.237  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.909  -0.176  -0.152  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.508   0.035  -0.039  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.313   0.233   0.069  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.094   0.488   0.209  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.949  -0.490  -0.023  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.374  -0.240   0.116  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.237  -1.143  -0.094  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.819   1.006   0.487  0.00  0.00           O+0
HETATM   12  H   UNK     0       1.502   1.446   0.497  0.00  0.00           H+0
HETATM   13  H   UNK     0       1.576  -1.472  -0.316  0.00  0.00           H+0
HETATM   14  H   UNK     0       3.467   1.884   0.161  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   14                                                       
CONECT   12    7                                                            
CONECT   13    8                                                            
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END
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3D PDB for NP0004881 (Diatretyne 2)

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SMILES for NP0004881 (Diatretyne 2)
[H]OC(=O)C(\[H])=C(/[H])C#CC#CC#N
Download
INCHI for NP0004881 (Diatretyne 2)
InChI=1S/C8H3NO2/c9-7-5-3-1-2-4-6-8(10)11/h4,6H,(H,10,11)/b6-4+
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View in JSmolView NMR Assignments
Synonyms
ValueSource
7-Cyano-(e)-2-heptene-4,6-diynoic acidHMDB
7-Cyano-2-heptene-4,6-diynoic acidHMDB
7-Cyano-trans-2-heptene-4,6-diynoic acidHMDB
Diatretyne 2HMDB
Diatretyne IIHMDB
DiatretynnitrilHMDB
Nudic acid bHMDB
(2E)-7-Cyanohept-2-en-4,6-diynoateHMDB
Chemical FormulaC8H3NO2
Average Mass145.1149 Da
Monoisotopic Mass145.01638 Da
IUPAC Name(2E)-7-cyanohept-2-en-4,6-diynoic acid
Traditional Name(2E)-7-cyanohept-2-en-4,6-diynoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)\C=C\C#CC#CC#N
InChI Identifier
InChI=1S/C8H3NO2/c9-7-5-3-1-2-4-6-8(10)11/h4,6H,(H,10,11)/b6-4+
InChI KeyDMGKNZBGIHCAMP-GQCTYLIASA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Camarophyllus virgineus-
ClitocybeNPAtlas
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentMedium-chain fatty acids  
Alternative Parents
Substituents
  • Medium-chain fatty acid
    • 

  • Amino fatty acid
    • 

  • Unsaturated fatty acid
    • 

  • Straight chain fatty acid
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carbonitrile
    • 

  • Nitrile
    • 

  • Organic nitrogen compound
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility44210 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.32ALOGPS
logP1.28ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)2.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area61.09 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity40.79 m³·mol⁻¹ChemAxon
Polarizability14.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA009793  
HMDB IDHMDB0031004  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002993  
KNApSAcK IDC00054127  
Chemspider ID4938371  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6433188  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDrw1824141  
References
General References
  1. ANCHEL M: Structure of diatretyne 2, an antibiotic polyacetylenic nitrile from Clitocybe diatreta. Science. 1955 Apr 22;121(3147):607-8. doi: 10.1126/science.121.3147.607. [PubMed:14372966  ]