NP-MRD: Showing NP-Card for Achimillic acid C (NP0085505)

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Record Information

Version

2.0

Created at

2022-04-29 06:00:32 UTC

Updated at

2022-04-29 06:00:33 UTC

NP-MRD ID

NP0085505

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Achimillic acid C

Description

(3R)-3-{[(1E,2S)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-ylidene]methyl}-2-methylidene-6-oxoheptanoic acid belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. Achimillic acid C is found in Achillea millefolium . Based on a literature review very few articles have been published on (3R)-3-{[(1E,2S)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-ylidene]methyl}-2-methylidene-6-oxoheptanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 38  0  0  0  0  0  0  0  0999 V2000
   -0.5865   -3.0333    0.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8341   -1.9252   -0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7247   -2.0523   -1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -3.1777   -1.4940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0736   -1.0257   -2.0471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1645   -0.6536    0.2485 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5038   -0.1475   -0.9432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8344    0.0377   -0.9559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5549    0.5389   -2.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0232    0.8652   -3.2306 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9578    0.5918   -1.7584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1147    0.1789   -0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232   -0.1944    0.0774 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6456    0.7097    1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9484   -1.5265    0.4608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814    0.2637    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634    0.8035    0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0217    1.7539    1.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2239    2.3985    0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    1.9452    2.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179   -2.9208    1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0761   -3.9457    0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9294   -1.1468   -3.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6397   -0.8785    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0749    0.0824   -1.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7658    0.9256   -2.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1085    0.1211   -0.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5715    1.3235    1.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4439    0.1594    2.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376    1.4545    1.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9172   -1.5731    1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5140    1.1578    1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -0.2348    1.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110    1.3183   -0.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0229   -0.0378    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1518    3.5240    0.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4571    2.1711   -0.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1476    2.1492    1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  2  0
 18 17  1  0
 17 16  1  0
 16  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
  6  2  1  0
  2  1  2  3
  2  3  1  0
  3  5  1  0
  3  4  2  0
 13  8  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 17 34  1  0
 17 35  1  0
 16 32  1  0
 16 33  1  0
  6 24  1  1
  7 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
M  END


  Mrv1652304292208002D          

 20 20  0  0  1  0            999 V2000
    0.1190    4.0753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880    3.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0235    3.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8440    3.2363    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8440    2.4113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6645    3.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155    4.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3011    4.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110    2.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0235    1.7211    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8485    1.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2610    1.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0860    1.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4985    0.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4985    1.7211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110    1.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2140    1.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6265    1.7211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6265    0.2922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0235    0.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  6  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  3  9  2  0  0  0  0
 10  9  1  6  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
 13 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 16 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0085505

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CC[C@H](\C=C1\C(=O)C=C[C@]1(C)O)C(=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O5/c1-9(16)4-5-11(10(2)14(18)19)8-12-13(17)6-7-15(12,3)20/h6-8,11,20H,2,4-5H2,1,3H3,(H,18,19)/b12-8-/t11-,15+/m1/s1

> <INCHI_KEY>
ARZDSTJTDVJYCF-AZCASUJJSA-N

> <FORMULA>
C15H18O5

> <MOLECULAR_WEIGHT>
278.304

> <EXACT_MASS>
278.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.22163607163121

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-3-{[(1E,2S)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-ylidene]methyl}-2-methylidene-6-oxoheptanoic acid

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
1.2908081929999997

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.815826822688074

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.449991008608951

> <JCHEM_PKA_STRONGEST_BASIC>
-3.31688262965025

> <JCHEM_POLAR_SURFACE_AREA>
91.66999999999999

> <JCHEM_REFRACTIVITY>
75.00319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-{[(1E,2S)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-ylidene]methyl}-2-methylidene-6-oxoheptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       0.222   7.607   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.284   7.287   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.911   5.880   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.442   6.041   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.442   4.501   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.974   5.880   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.762   7.547   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.429   8.317   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.141   4.546   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.911   3.213   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.451   3.213   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.221   1.879   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.761   1.879   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.531   0.545   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.531   3.213   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.141   1.879   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.399   1.879   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.169   3.213   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.169   0.545   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.911   0.545   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4    8                                                       
CONECT    8    7    2                                                       
CONECT    9    3   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
(3R)-3-{[(1E,2S)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-ylidene]methyl}-2-methylidene-6-oxoheptanoate	Generator

Chemical Formula

C₁₅H₁₈O₅

Average Mass

278.3040 Da

Monoisotopic Mass

278.11542 Da

IUPAC Name

(3R)-3-{[(1E,2S)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-ylidene]methyl}-2-methylidene-6-oxoheptanoic acid

Traditional Name

(3R)-3-{[(1E,2S)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-ylidene]methyl}-2-methylidene-6-oxoheptanoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)CC[C@H](\C=C1\C(=O)C=C[C@]1(C)O)C(=C)C(O)=O

InChI Identifier

InChI=1S/C15H18O5/c1-9(16)4-5-11(10(2)14(18)19)8-12-13(17)6-7-15(12,3)20/h6-8,11,20H,2,4-5H2,1,3H3,(H,18,19)/b12-8-/t11-,15+/m1/s1

InChI Key

ARZDSTJTDVJYCF-AZCASUJJSA-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
Achillea millefolium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents

Substituents

Medium-chain keto acid
Branched fatty acid
Hydroxy fatty acid
Fatty acyl
Unsaturated fatty acid
Tertiary alcohol
Ketone
Cyclic ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

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	1.24	ALOGPS
logP	1.29	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	4.45	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	75 m³·mol⁻¹	ChemAxon
Polarizability	28.22 Å³	ChemAxon
Number of Rings	1	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

C00055387

Chemspider ID

8237642

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10062090

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Achimillic acid C (NP0085505)

MOL for NP0085505 (Achimillic acid C)

3D MOL for NP0085505 (Achimillic acid C)

3D SDF for NP0085505 (Achimillic acid C)

3D-SDF for NP0085505 (Achimillic acid C)

PDB for NP0085505 (Achimillic acid C)

3D PDB for NP0085505 (Achimillic acid C)

SMILES for NP0085505 (Achimillic acid C)

INCHI for NP0085505 (Achimillic acid C)

Structure for NP0085505 (Achimillic acid C)

3D Structure for NP0085505 (Achimillic acid C)