NP-MRD: Showing NP-Card for minquartynoic acid (NP0169024)

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Record Information

Version

2.0

Created at

2022-09-03 04:54:49 UTC

Updated at

2022-09-03 04:54:49 UTC

NP-MRD ID

NP0169024

Secondary Accession Numbers

None

Natural Product Identification

Common Name

minquartynoic acid

Description

Minquartynoic acid, also known as (S)-minquartynoate, 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. minquartynoic acid is found in Coula edulis, Minquartia guianensis and Ochanostachys amentacea. minquartynoic acid was first documented in 2000 (PMID: 11000043). Based on a literature review a small amount of articles have been published on minquartynoic acid (PMID: 11547419) (PMID: 12123365).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 40  0  0  0  0  0  0  0  0999 V2000
   10.3325    0.3471   -3.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1417    0.2556   -1.6338 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8808   -0.8108   -1.1732 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7193    0.1447   -1.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5377    0.0733   -1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1560    0.0013   -0.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9709   -0.0503   -0.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5774   -0.1001   -0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3877   -0.1418   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9884   -0.1884    0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119   -0.2228    0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6682   -0.2678    0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0681   -0.0752    1.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5636   -0.1254    2.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2497    0.9472    1.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7451    0.8870    1.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3414   -0.4208    1.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1091   -0.7387   -0.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6830    0.2289   -1.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4968    0.1055   -2.4974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4310    1.2853   -0.8142 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4006    0.3702   -3.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7904   -0.4765   -3.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8238    1.2850   -3.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4995    1.2242   -1.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6737   -0.5654   -0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806    0.5273   -0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0221   -1.2735    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5267   -0.7444    2.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7573    0.9747    2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7408    0.1240    3.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9038   -1.1334    1.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9306    1.9732    1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0219    0.9079    0.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9351    0.9907    2.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2358    1.7540    1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9017   -1.2281    1.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4502   -0.4384    1.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0003   -0.8469   -0.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5642   -1.7360   -0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2413    1.2074   -0.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  3  0
  5  6  1  0
  6  7  3  0
  7  8  1  0
  8  9  3  0
  9 10  1  0
 10 11  3  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 21  1  0
 19 20  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  1
  3 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 21 41  1  0
M  END

  Mrv1652309032206542D          

 21 20  0  0  1  0            999 V2000
   -4.1467   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322   -1.1566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4322   -1.9816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    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
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    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  1  0  0  0
  2  4  1  0  0  0  0
  4  5  3  0  0  0  0
  5  6  1  0  0  0  0
  6  7  3  0  0  0  0
  7  8  1  0  0  0  0
  8  9  3  0  0  0  0
  9 10  1  0  0  0  0
 10 11  3  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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0169024

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)C#CC#CC#CC#CCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O3/c1-17(19)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18(20)21/h17,19H,4,6,8,10,12,14,16H2,1H3,(H,20,21)/t17-/m0/s1

> <INCHI_KEY>
MTWGWIOCIREVRF-KRWDZBQOSA-N

> <FORMULA>
C18H20O3

> <MOLECULAR_WEIGHT>
284.355

> <EXACT_MASS>
284.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
34.71986074000131

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(17S)-17-hydroxyoctadeca-9,11,13,15-tetraynoic acid

> <ALOGPS_LOGP>
4.20

> <JCHEM_LOGP>
4.1757819693333325

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.251490994381232

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.525879787407715

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5635978394149648

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
85.32369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
minquartynoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      -7.740  -1.389   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.407  -2.159   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.407  -3.699   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -5.073  -1.389   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.739  -0.619   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.406   0.151   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.072   0.921   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.262   1.691   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.595   2.461   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.929   3.231   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      14.932   2.461   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                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
(-)-Minquartynoic acid	ChEBI
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid	ChEBI
(S)-Minquartynoic acid	ChEBI
Minquartic acid	ChEBI
(-)-Minquartynoate	Generator
(S)-17-Hydroxy-9,11,13,15-octadecatetraynoate	Generator
(S)-Minquartynoate	Generator
Minquartate	Generator
Minquartynoate	Generator
(S)-(-)-(e)-15,16-Dihydrominquartynoic acid	MeSH

Chemical Formula

C₁₈H₂₀O₃

Average Mass

284.3550 Da

Monoisotopic Mass

284.14124 Da

IUPAC Name

(17S)-17-hydroxyoctadeca-9,11,13,15-tetraynoic acid

Traditional Name

minquartynoic acid

CAS Registry Number

Not Available

SMILES

C[C@H](O)C#CC#CC#CC#CCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H20O3/c1-17(19)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18(20)21/h17,19H,4,6,8,10,12,14,16H2,1H3,(H,20,21)/t17-/m0/s1

InChI Key

MTWGWIOCIREVRF-KRWDZBQOSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Coula edulis	LOTUS Database	35616633
Minquartia guianensis	LOTUS Database	35616633
Ochanostachys amentacea	LOTUS Database	35616633

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
Hydroxy fatty acid
Unsaturated fatty acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:542606 )
polyunsaturated fatty acid (CHEBI:542606 )
straight-chain fatty acid (CHEBI:542606 )
acetylenic fatty acid (CHEBI:542606 )
hydroxy fatty acid (CHEBI:542606 )
tetrayne (CHEBI:542606 )

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	4.2	ALOGPS
logP	4.18	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.53	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	85.32 m³·mol⁻¹	ChemAxon
Polarizability	34.72 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

C00046157

Chemspider ID

159656

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

183614

PDB ID

Not Available

ChEBI ID

542606

Good Scents ID

rw1873311

References

General References

Rasmussen HB, Christensen SB, Kvist LP, Kharazmi A, Huansi AG: Absolute configuration and antiprotozoal activity of minquartynoic acid. J Nat Prod. 2000 Sep;63(9):1295-6. doi: 10.1021/np990604k. [PubMed:11000043 ]
Rashid MA, Gustafson KR, Cardellina JH 2nd, Boyd MR: Absolute stereochemistry and anti-HIV activity of minquartynoic acid, a polyacetylene from Ochanostachys amentacea. Nat Prod Lett. 2001;15(1):21-6. doi: 10.1080/10575630108041253. [PubMed:11547419 ]
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LOTUS database [Link]

Showing NP-Card for minquartynoic acid (NP0169024)

MOL for NP0169024 (minquartynoic acid)

3D MOL for NP0169024 (minquartynoic acid)

3D SDF for NP0169024 (minquartynoic acid)

3D-SDF for NP0169024 (minquartynoic acid)

PDB for NP0169024 (minquartynoic acid)

3D PDB for NP0169024 (minquartynoic acid)

SMILES for NP0169024 (minquartynoic acid)

INCHI for NP0169024 (minquartynoic acid)

Structure for NP0169024 (minquartynoic acid)

3D Structure for NP0169024 (minquartynoic acid)