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Showing NP-Card for alpha-Dimorphecolic acid (NP0333830)

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Record Information
Version2.0
Created at2024-09-09 20:44:03 UTC
Updated at2024-09-09 20:44:03 UTC
NP-MRD IDNP0333830
Secondary Accession NumbersNone
Natural Product Identification
Common Namealpha-Dimorphecolic acid
DescriptionPresent in plant and animal lipids as autoxidn. Or lipoxygenase oxidn. Production of linoleic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0333830 (alpha-Dimorphecolic acid)


  Mrv2104 05242323162D          

 25 24  0  0  0  0            999 V2000
    5.6645    8.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    5.7454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    4.0954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    2.8579    0.0000 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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6 22  1  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 23  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 24  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 25  1  0  0  0  0
 14 17  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 18 21  1  0  0  0  0
M  END
Download

3D MOL for NP0333830 (alpha-Dimorphecolic acid)

Download
3D SDF for NP0333830 (alpha-Dimorphecolic acid)

  Mrv2104 05242323162D          

 25 24  0  0  0  0            999 V2000
    5.6645    8.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    5.7454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    4.0954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    2.8579    0.0000 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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6 22  1  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 23  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 24  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 25  1  0  0  0  0
 14 17  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 18 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333830

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])C(O)CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+

> <INCHI_KEY>
NPDSHTNEKLQQIJ-ZJHFMPGANA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.451

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.329084914745394

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid

> <JCHEM_LOGP>
5.191065727333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.795677864657474

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.676745528848431

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5759708475080179

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
90.03429999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0333830 (alpha-Dimorphecolic acid)
Download
PDB for NP0333830 (alpha-Dimorphecolic acid)
HEADER    PROTEIN                                 24-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-MAY-23         0                                  
HETATM    1  C   UNK     0      10.574  15.345   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.240  14.575   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.240  13.035   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.906  12.265   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.906  10.725   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.573   9.955   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.573   8.415   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.906   7.645   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.240   3.795   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      21.243   6.105   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      19.909   3.795   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       5.239  10.725   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       5.239   7.645   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       9.240   8.415   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       6.573   5.335   0.000  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   22    8                                                  
CONECT    7    9   10                                                       
CONECT    8    6   23   11                                                  
CONECT    9    7   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   24   14                                                  
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   25   17                                                  
CONECT   15   12   17                                                       
CONECT   16   13   18                                                       
CONECT   17   14   15   19                                                  
CONECT   18   16   20   21                                                  
CONECT   19   17                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22    6                                                            
CONECT   23    8                                                            
CONECT   24   11                                                            
CONECT   25   14                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

Download
3D PDB for NP0333830 (alpha-Dimorphecolic acid)
Download
SMILES for NP0333830 (alpha-Dimorphecolic acid)
[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])C(O)CCCCCCCC(O)=O
Download
INCHI for NP0333830 (alpha-Dimorphecolic acid)
InChI=1/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+
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View in JSmol
Synonyms
ValueSource
a-DimorphecolateGenerator
a-Dimorphecolic acidGenerator
alpha-DimorphecolateGenerator
Α-dimorphecolateGenerator
Α-dimorphecolic acidGenerator
Chemical FormulaC18H32O3
Average Mass296.4510 Da
Monoisotopic Mass296.23514 Da
IUPAC Name(10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid
Traditional Name(10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCC)=C(/[H])\C(\[H])=C(/[H])C(O)CCCCCCCC(O)=O
InChI Identifier
InChI=1/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+
InChI KeyNPDSHTNEKLQQIJ-ZJHFMPGANA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassLineolic acids and derivatives  
Direct ParentLineolic acids and derivatives  
Alternative Parents
Substituents
  • Octadecanoid
    • 

  • Long-chain fatty acid
    • 

  • Hydroxy fatty acid
    • 

  • Fatty acid
    • 

  • Unsaturated fatty acid
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.19ChemAxon
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity90.03 m³·mol⁻¹ChemAxon
Polarizability37.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Swain SS, Paidesetty SK, Padhy RN: Antibacterial, antifungal and antimycobacterial compounds from cyanobacteria. Biomed Pharmacother. 2017 Jun;90:760-776. doi: 10.1016/j.biopha.2017.04.030. Epub 2017 Apr 15. [PubMed:28419973  ] 
  2. Gurnani M, Rath P, Chauhan A, Ranjan A, Ghosh A, Lal R, Mukerjee N, Aljarba NH, Alkahtani S, Rajput VD, Sushkova S, Prazdnova EV, Minkina T, Jindal T: Inhibition of Filamentous Thermosensitive Mutant-Z Protein in Bacillus subtilis by Cyanobacterial Bioactive Compounds. Molecules. 2022 Mar 15;27(6). pii: molecules27061907. doi: 10.3390/molecules27061907. [PubMed:35335270  ] 
  3. Zhuo G, Wang L, Ali M, Jing Z, Hassan MF: Effect of hexavalent chromium on growth performance and metabolism in broiler chicken. Front Vet Sci. 2023 Sep 26;10:1273944. doi: 10.3389/fvets.2023.1273944.  eCollection 2023. [PubMed:37822955  ] 
  4. Lin Y, Yan G, Feng F, Wang M, Long F: Characterization of intestinal microbiota and serum metabolites in patients with mild hepatic encephalopathy. Open Life Sci. 2022 Mar 10;17(1):139-154. doi: 10.1515/biol-2021-0140.  eCollection 2022. [PubMed:35350446  ] 
  5. Yoon JY, Kim JH, Baek KS, Kim GS, Lee SE, Lee DY, Choi JH, Kim SY, Park HB, Sung GH, Lee KR, Cho JY, Noh HJ: A direct protein kinase B-targeted anti-inflammatory activity of cordycepin from artificially cultured fruit body of Cordyceps militaris. Pharmacogn Mag. 2015 Jul-Sep;11(43):477-85. doi: 10.4103/0973-1296.160454. [PubMed:26246722  ]