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Showing NP-Card for aurantoic acid (NP0182565)

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Record Information
Version2.0
Created at2022-09-03 21:17:28 UTC
Updated at2022-09-03 21:17:28 UTC
NP-MRD IDNP0182565
Secondary Accession NumbersNone
Natural Product Identification
Common Nameaurantoic acid
DescriptionAurantoic acid, also known as aurantoate, 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. aurantoic acid is found in Theonella swinhoei. aurantoic acid was first documented in 2009 (PMID: 19961178). Based on a literature review very few articles have been published on Aurantoic acid (PMID: 31529277).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0182565 (aurantoic acid)


  Mrv1652309032223172D          

 15 14  0  0  0  0            999 V2000
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    2.1434    0.0000 Cl  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
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
Download

3D MOL for NP0182565 (aurantoic acid)

     RDKit          3D

 28 27  0  0  0  0  0  0  0  0999 V2000
    3.2708    3.7962    4.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7321    2.4220    3.9670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9508    1.0788    4.9710 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0203    2.2807    2.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3822    1.1353    2.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8227    0.2919    1.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1435   -0.7331    1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461   -0.4505   -0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0562   -1.4367   -0.8824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4637   -1.1535   -2.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1976   -2.1739   -2.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5329   -1.9120   -4.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2910   -2.8889   -4.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6396   -3.9208   -4.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5382   -2.5864   -6.2911 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3596    3.7380    4.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7772    4.5622    3.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767    3.9840    5.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9390    3.2346    2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3538    0.2681    2.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4682   -0.2927    2.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0298   -1.7289    1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842    0.5301   -0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3027   -2.4090   -0.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2181   -0.1905   -2.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4569   -3.0880   -2.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2597   -0.9868   -4.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7800   -2.4153   -6.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 15 28  1  0
M  END
Download

3D SDF for NP0182565 (aurantoic acid)


  Mrv1652309032223172D          

 15 14  0  0  0  0            999 V2000
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    2.1434    0.0000 Cl  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
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0182565

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(Cl)=C\C=C\C=C\C=C\C=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H13ClO2/c1-11(13)9-7-5-3-2-4-6-8-10-12(14)15/h2-10H,1H3,(H,14,15)/b3-2+,6-4+,7-5+,10-8+,11-9-

> <INCHI_KEY>
XUUUHVRPNJADCG-HKNGRZMZSA-N

> <FORMULA>
C12H13ClO2

> <MOLECULAR_WEIGHT>
224.68

> <EXACT_MASS>
224.0604074

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
24.63450742434884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E,10Z)-11-chlorododeca-2,4,6,8,10-pentaenoic acid

> <JCHEM_LOGP>
3.0313468896666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.884221256661797

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
69.1865

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
aurantoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0182565 (aurantoic acid)

Download
PDB for NP0182565 (aurantoic acid)
HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.780   5.335   0.000  0.00  0.00           C+0
HETATM    3 Cl   UNK     0      11.550   4.001   0.000  0.00  0.00          Cl+0
HETATM    4  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.310  -1.334   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                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

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3D PDB for NP0182565 (aurantoic acid)
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SMILES for NP0182565 (aurantoic acid)
C\C(Cl)=C\C=C\C=C\C=C\C=C\C(O)=O
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INCHI for NP0182565 (aurantoic acid)
InChI=1S/C12H13ClO2/c1-11(13)9-7-5-3-2-4-6-8-10-12(14)15/h2-10H,1H3,(H,14,15)/b3-2+,6-4+,7-5+,10-8+,11-9-
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View in JSmol
Synonyms
ValueSource
AurantoateGenerator
Chemical FormulaC12H13ClO2
Average Mass224.6800 Da
Monoisotopic Mass224.06041 Da
IUPAC Name(2E,4E,6E,8E,10Z)-11-chlorododeca-2,4,6,8,10-pentaenoic acid
Traditional Nameaurantoic acid
CAS Registry NumberNot Available
SMILES
C\C(Cl)=C\C=C\C=C\C=C\C=C\C(O)=O
InChI Identifier
InChI=1S/C12H13ClO2/c1-11(13)9-7-5-3-2-4-6-8-10-12(14)15/h2-10H,1H3,(H,14,15)/b3-2+,6-4+,7-5+,10-8+,11-9-
InChI KeyXUUUHVRPNJADCG-HKNGRZMZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Theonella swinhoeiLOTUS Database
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
    • 

  • Halogenated fatty acid
    • 

  • Unsaturated fatty acid
    • 

  • Chloroalkene
    • 

  • Haloalkene
    • 

  • Vinyl halide
    • 

  • Vinyl chloride
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organochloride
    • 

  • Organohalogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP3.03ChemAxon
pKa (Strongest Acidic)4.88ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.19 m³·mol⁻¹ChemAxon
Polarizability24.63 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24665878  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44614262  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Angawi RF, Calcinai B, Cerrano C, Dien HA, Fattorusso E, Scala F, Taglialatela-Scafati O: Dehydroconicasterol and aurantoic acid, a chlorinated polyene derivative, from the Indonesian sponge Theonella swinhoei. J Nat Prod. 2009 Dec;72(12):2195-8. doi: 10.1021/np900669d. [PubMed:19961178  ] 
  2. Han KY, Wu X, Jiang C, Huang R, Li ZH, Feng T, Chen HP, Liu JK: Three New Compounds from the Actinomycete Actinocorallia aurantiaca. Nat Prod Bioprospect. 2019 Oct;9(5):351-354. doi: 10.1007/s13659-019-00217-0.  Epub 2019 Sep 16. [PubMed:31529277  ] 
  3. LOTUS database [Link]