NP-MRD: Showing NP-Card for (E)-7-Methoxytetradec-4-enoic acid (NP0069398)

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Record Information

Version

2.0

Created at

2022-04-28 14:44:53 UTC

Updated at

2022-04-28 14:44:53 UTC

NP-MRD ID

NP0069398

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(E)-7-Methoxytetradec-4-enoic acid

Description

Lyngbic acid, also known as lyngbate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. (E)-7-Methoxytetradec-4-enoic acid is found in Lyngbya majuscula. (E)-7-Methoxytetradec-4-enoic acid was first documented in 2016 (PMID: 26495995). Based on a literature review a small amount of articles have been published on Lyngbic acid (PMID: 27426414) (PMID: 30444349) (PMID: 31978978) (PMID: 29791035).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 45  0  0  0  0  0  0  0  0999 V2000
   -6.5321   -1.2890    2.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0997   -0.9825    1.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0284   -1.1758    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6449   -0.8967   -0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2247    0.5238   -0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8477    0.8258   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7734   -0.0595    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5392    0.3507   -0.5545 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6932   -0.4762   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9277    0.0059   -0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299    0.4925    0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1435    0.9621   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3397    0.1748   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6116    0.3097    1.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9012    1.0474    1.9399 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6681   -0.3877    1.7900 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4384    0.2389   -1.9316 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5594    1.4389   -2.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1783   -0.5385    1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8007   -2.3283    1.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5395   -1.1249    3.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3842   -1.6633    2.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9276    0.0750    2.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7907   -0.5258   -0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3051   -2.2156   -0.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9551   -1.6354    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6490   -1.0706   -1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9147    1.2521   -0.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2181    0.6859    1.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9069    0.6489   -1.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5730    1.8836   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0070   -1.1305   -0.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7957    0.1039    1.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6922    1.4290   -0.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7560   -0.4782    1.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5116   -1.5221   -0.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0094   -0.0406   -1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8147    0.5274    1.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2991    2.0451   -0.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885    0.8737   -1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2477    0.4978   -0.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2349   -0.9091   -0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9546   -1.2475    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5488    1.9084   -2.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2036    2.1795   -2.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909    1.2171   -3.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
  8 17  1  0
 17 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  6
  9 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 16 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
M  END


  Mrv1652304282216442D          

 18 17  0  0  1  0            999 V2000
    8.7987   -5.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3388   -6.3787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9886   -5.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4485   -5.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6384   -5.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0983   -4.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2882   -4.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481   -4.3519    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9379   -4.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979   -3.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877   -4.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476   -3.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6974   -2.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1127   -3.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181   -3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8283   -3.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0688   -4.9755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  6  0  0  0
 16 17  1  0  0  0  0
  1 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069398

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC[C@@H](C\C=C\CCC(O)=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C15H28O3/c1-3-4-5-6-8-11-14(18-2)12-9-7-10-13-15(16)17/h7,9,14H,3-6,8,10-13H2,1-2H3,(H,16,17)/b9-7+/t14-/m0/s1

> <INCHI_KEY>
DHIPOEWPWSLXNL-KGXGESDWSA-N

> <FORMULA>
C15H28O3

> <MOLECULAR_WEIGHT>
256.386

> <EXACT_MASS>
256.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
31.883092330888633

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4E,7S)-7-methoxytetradec-4-enoic acid

> <ALOGPS_LOGP>
5.10

> <JCHEM_LOGP>
4.261931767666666

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.710487110246528

> <JCHEM_PKA_STRONGEST_BASIC>
-4.124757856465959

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
75.4189

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.07e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lyngbic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      16.424 -10.743   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      17.432 -11.907   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.912 -11.034   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.904  -9.870   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.392 -10.161   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.383  -8.997   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.871  -9.288   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.863  -8.124   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.351  -8.415   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.343  -7.250   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.830  -7.541   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.822  -6.377   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.310  -6.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.302  -5.504   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.210  -5.795   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.367  -6.668   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.879  -6.377   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.928  -9.288   0.000  0.00  0.00           O+0
CONECT    1    2    3   18                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    8   17                                                       
CONECT   17   16                                                            
CONECT   18    1                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
Lyngbate	Generator
7S-Methoxytetradec-4(e)-enoic acid	MeSH

Chemical Formula

C₁₅H₂₈O₃

Average Mass

256.3860 Da

Monoisotopic Mass

256.20384 Da

IUPAC Name

(4E,7S)-7-methoxytetradec-4-enoic acid

Traditional Name

lyngbic acid

CAS Registry Number

Not Available

SMILES

CCCCCCC[C@@H](C\C=C\CCC(O)=O)OC

InChI Identifier

InChI=1S/C15H28O3/c1-3-4-5-6-8-11-14(18-2)12-9-7-10-13-15(16)17/h7,9,14H,3-6,8,10-13H2,1-2H3,(H,16,17)/b9-7+/t14-/m0/s1

InChI Key

DHIPOEWPWSLXNL-KGXGESDWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Lyngbya majuscula	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:67609 )

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
logP	5.1	ALOGPS
logP	4.26	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.71	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	75.42 m³·mol⁻¹	ChemAxon
Polarizability	31.88 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9240201

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11065049

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sabry OM, Goeger DE, Gerwick WH: Biologically active new metabolites from a Florida collection of Moorea producens. Nat Prod Res. 2017 Mar;31(5):555-561. doi: 10.1080/14786419.2016.1207074. Epub 2016 Jul 18. [PubMed:27426414 ]
Moss NA, Leao T, Rankin MR, McCullough TM, Qu P, Korobeynikov A, Smith JL, Gerwick L, Gerwick WH: Ketoreductase Domain Dysfunction Expands Chemodiversity: Malyngamide Biosynthesis in the Cyanobacterium Okeania hirsuta. ACS Chem Biol. 2018 Dec 21;13(12):3385-3395. doi: 10.1021/acschembio.8b00910. Epub 2018 Dec 3. [PubMed:30444349 ]
Kawaguchi M, Satake M, Zhang BT, Xiao YY, Fukuoka M, Uchida H, Nagai H: Neo-Aplysiatoxin A Isolated from Okinawan Cyanobacterium Moorea Producens. Molecules. 2020 Jan 22;25(3). pii: molecules25030457. doi: 10.3390/molecules25030457. [PubMed:31978978 ]
Engene N, Tronholm A, Paul VJ: Uncovering cryptic diversity of Lyngbya: the new tropical marine cyanobacterial genus Dapis (Oscillatoriales). J Phycol. 2018 Aug;54(4):435-446. doi: 10.1111/jpy.12752. Epub 2018 Jun 25. [PubMed:29791035 ]
Meyer JL, Gunasekera SP, Scott RM, Paul VJ, Teplitski M: Microbiome shifts and the inhibition of quorum sensing by Black Band Disease cyanobacteria. ISME J. 2016 May;10(5):1204-16. doi: 10.1038/ismej.2015.184. Epub 2015 Oct 23. [PubMed:26495995 ]

Showing NP-Card for (E)-7-Methoxytetradec-4-enoic acid (NP0069398)

MOL for NP0069398 ((E)-7-Methoxytetradec-4-enoic acid)

3D MOL for NP0069398 ((E)-7-Methoxytetradec-4-enoic acid)

3D SDF for NP0069398 ((E)-7-Methoxytetradec-4-enoic acid)

3D-SDF for NP0069398 ((E)-7-Methoxytetradec-4-enoic acid)

PDB for NP0069398 ((E)-7-Methoxytetradec-4-enoic acid)

3D PDB for NP0069398 ((E)-7-Methoxytetradec-4-enoic acid)

SMILES for NP0069398 ((E)-7-Methoxytetradec-4-enoic acid)

INCHI for NP0069398 ((E)-7-Methoxytetradec-4-enoic acid)

Structure for NP0069398 ((E)-7-Methoxytetradec-4-enoic acid)

3D Structure for NP0069398 ((E)-7-Methoxytetradec-4-enoic acid)