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Showing NP-Card for 9S,12R,13S-Trihydroxy-10E,15Z-octadecadienoic acid (NP0050305)

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Record Information
Version2.0
Created at2022-04-27 20:52:09 UTC
Updated at2022-04-27 20:52:09 UTC
NP-MRD IDNP0050305
Secondary Accession NumbersNone
Natural Product Identification
Common Name9S,12R,13S-Trihydroxy-10E,15Z-octadecadienoic acid
DescriptionMalyngic acid, also known as malyngate, 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. 9S,12R,13S-Trihydroxy-10E,15Z-octadecadienoic acid is found in Lyngbya majuscula. 9S,12R,13S-Trihydroxy-10E,15Z-octadecadienoic acid was first documented in 2020 (PMID: 33078401). Based on a literature review very few articles have been published on Malyngic acid.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050305 (9S,12R,13S-Trihydroxy-10E,15Z-octadecadienoic acid)


  Mrv1652304272222522D          

 23 22  0  0  1  0            999 V2000
    9.9513    3.2704    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
    8.5224    3.2704    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
    7.0934    3.2704    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
    5.6645    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  1  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
    4.2355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    4.5079    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5211    5.3329    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2355    5.7454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    4.0954    0.0000 O   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
   10.6658    2.8579    0.0000 C   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
  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  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 19  1  1  0  0  0
  8 20  1  6  0  0  0
  1 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
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3D MOL for NP0050305 (9S,12R,13S-Trihydroxy-10E,15Z-octadecadienoic acid)

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3D SDF for NP0050305 (9S,12R,13S-Trihydroxy-10E,15Z-octadecadienoic acid)

  Mrv1652304272222522D          

 23 22  0  0  1  0            999 V2000
    9.9513    3.2704    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
    8.5224    3.2704    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
    7.0934    3.2704    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
    5.6645    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  1  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
    4.2355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    4.5079    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5211    5.3329    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2355    5.7454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    4.0954    0.0000 O   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
   10.6658    2.8579    0.0000 C   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
  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  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 19  1  1  0  0  0
  8 20  1  6  0  0  0
  1 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050305

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h3,7,13-17,19-21H,2,4-6,8-12H2,1H3,(H,22,23)/b7-3-,14-13+/t15-,16-,17+/m0/s1

> <INCHI_KEY>
MKYUCBXUUSZMQB-OADLNGDBSA-N

> <FORMULA>
C18H32O5

> <MOLECULAR_WEIGHT>
328.449

> <EXACT_MASS>
328.22497413

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.78918546991639

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S,10E,12R,13S,15Z)-9,12,13-trihydroxyoctadeca-10,15-dienoic acid

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
2.8853510533333324

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.61089337317524

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.676745182833833

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8471940908473607

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
92.91129999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S,10E,12R,13S,15Z)-9,12,13-trihydroxyoctadeca-10,15-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050305 (9S,12R,13S-Trihydroxy-10E,15Z-octadecadienoic acid)
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PDB for NP0050305 (9S,12R,13S-Trihydroxy-10E,15Z-octadecadienoic acid)
HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.906   7.645   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.573   8.415   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.573   9.955   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.906  10.725   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.239  10.725   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.239  12.265   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.905  13.035   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.572  12.265   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.238  13.035   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.239   7.645   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.240   3.795   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      21.243   6.105   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      19.909   3.795   0.000  0.00  0.00           O+0
CONECT    1    2   21                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   11                                                            
CONECT   20    8                                                            
CONECT   21    1   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

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3D PDB for NP0050305 (9S,12R,13S-Trihydroxy-10E,15Z-octadecadienoic acid)
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SMILES for NP0050305 (9S,12R,13S-Trihydroxy-10E,15Z-octadecadienoic acid)
CC\C=C/C[C@H](O)[C@H](O)\C=C\[C@@H](O)CCCCCCCC(O)=O
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INCHI for NP0050305 (9S,12R,13S-Trihydroxy-10E,15Z-octadecadienoic acid)
InChI=1S/C18H32O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h3,7,13-17,19-21H,2,4-6,8-12H2,1H3,(H,22,23)/b7-3-,14-13+/t15-,16-,17+/m0/s1
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View in JSmol
Synonyms
ValueSource
MalyngateGenerator
Chemical FormulaC18H32O5
Average Mass328.4490 Da
Monoisotopic Mass328.22497 Da
IUPAC Name(9S,10E,12R,13S,15Z)-9,12,13-trihydroxyoctadeca-10,15-dienoic acid
Traditional Name(9S,10E,12R,13S,15Z)-9,12,13-trihydroxyoctadeca-10,15-dienoic acid
CAS Registry NumberNot Available
SMILES
CC\C=C/C[C@H](O)[C@H](O)\C=C\[C@@H](O)CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h3,7,13-17,19-21H,2,4-6,8-12H2,1H3,(H,22,23)/b7-3-,14-13+/t15-,16-,17+/m0/s1
InChI KeyMKYUCBXUUSZMQB-OADLNGDBSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lyngbya majuscula-
Chemical Taxonomy
Description 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
    • 

  • 1,2-diol
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Polyol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.65ALOGPS
logP2.89ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity92.91 m³·mol⁻¹ChemAxon
Polarizability38.79 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00000387  
Chemspider ID8124959  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9949348  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Luo M, Hu K, Zeng Q, Yang X, Wang Y, Dong L, Huang F, Zhang R, Su D: Comparative analysis of the morphological property and chemical composition of soluble and insoluble dietary fiber with bound phenolic compounds from different algae. J Food Sci. 2020 Nov;85(11):3843-3851. doi: 10.1111/1750-3841.15502. Epub 2020 Oct 19. [PubMed:33078401  ]