NP-MRD: Showing NP-Card for kermesic acid (NP0266532)

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Record Information

Version

2.0

Created at

2022-09-08 10:53:57 UTC

Updated at

2022-09-08 10:53:57 UTC

NP-MRD ID

NP0266532

Secondary Accession Numbers

None

Natural Product Identification

Common Name

kermesic acid

Description

Kermesic acid, also known as kermes or c.I. 75460, Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. kermesic acid was first documented in 2015 (PMID: 26515013). Kermesic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    2.2417   -1.0184   -1.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0403   -0.4132   -0.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0619   -0.0906    0.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4516   -0.3001   -0.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3314    0.0401    0.7979 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9388   -0.8365   -1.2086 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7858    0.4798    1.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8316    0.8164    2.3561 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5154    0.7252    1.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4734    0.3997    1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7214   -0.1610   -0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3991   -0.4877   -1.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -1.0018   -2.2122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769   -0.2162   -0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8036   -0.5426   -1.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7190   -1.0989   -2.7406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1146   -0.2661   -1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3385    0.2882    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6313    0.5522    0.5884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866    0.6223    1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6067    1.1793    2.2441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0020    0.3597    0.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.6876    1.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0269    1.2046    2.6232 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7377   -2.0348   -2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2712   -1.2172   -2.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8441   -0.3176   -2.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4868   -0.3339   -1.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6410    1.2258    3.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3165    1.1701    2.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746   -1.3746   -3.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9533   -0.5031   -1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8280    0.9697    1.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1191    1.4937    3.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  6  1  0
  4  5  2  0
  3  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 11  2  1  0
 22 14  1  0
 23 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
 21 34  1  0
M  END


  Mrv1533004241500382D          

 24 26  0  0  0  0            999 V2000
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  2 24  1  0  0  0  0
 10 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0266532

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C(O)=O)C(O)=CC2=C1C(=O)C1=C(O)C=C(O)C(O)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O8/c1-4-9-5(2-6(17)10(4)16(23)24)13(20)12-11(15(9)22)7(18)3-8(19)14(12)21/h2-3,17-19,21H,1H3,(H,23,24)

> <INCHI_KEY>
CXORMDKZEUMQHX-UHFFFAOYSA-N

> <FORMULA>
C16H10O8

> <MOLECULAR_WEIGHT>
330.248

> <EXACT_MASS>
330.037567282

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
30.4279300652478

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
3.8254490853333336

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.595610557592962

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2163657896270768

> <JCHEM_PKA_STRONGEST_BASIC>
-5.279925903195809

> <JCHEM_POLAR_SURFACE_AREA>
152.35999999999999

> <JCHEM_REFRACTIVITY>
81.37199999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   24                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   13   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    2   10                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
1-Methyl-2-carboxy-3,5,6,8-tetrahydroxyanthraquinone	ChEBI
C.I. 75460	ChEBI
C.I. natural red 3	ChEBI
Kermes	ChEBI
Natural red 3	ChEBI
Kermesate	Generator

Chemical Formula

C₁₆H₁₀O₈

Average Mass

330.2480 Da

Monoisotopic Mass

330.03757 Da

IUPAC Name

3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Traditional Name

3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=C(C(O)=O)C(O)=CC2=C1C(=O)C1=C(O)C=C(O)C(O)=C1C2=O

InChI Identifier

InChI=1S/C16H10O8/c1-4-9-5(2-6(17)10(4)16(23)24)13(20)12-11(15(9)22)7(18)3-8(19)14(12)21/h2-3,17-19,21H,1H3,(H,23,24)

InChI Key

CXORMDKZEUMQHX-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthracenecarboxylic acids and derivatives

Direct Parent

Anthracenecarboxylic acids

Alternative Parents

Substituents

Anthracene carboxylic acid
9,10-anthraquinone
Anthraquinone
Hydroxyanthraquinone
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
Hydroxybenzoic acid
Salicylic acid or derivatives
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.05	ALOGPS
logP	3.83	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	2.22	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	152.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	81.37 m³·mol⁻¹	ChemAxon
Polarizability	30.43 Å³	ChemAxon
Number of Rings	3	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11727234

PDB ID

Not Available

ChEBI ID

90183

Good Scents ID

Not Available

References

General References

Serrano A, van den Doel A, van Bommel M, Hallett J, Joosten I, van den Berg KJ: Investigation of crimson-dyed fibres for a new approach on the characterization of cochineal and kermes dyes in historical textiles. Anal Chim Acta. 2015 Oct 15;897:116-27. doi: 10.1016/j.aca.2015.09.046. Epub 2015 Oct 3. [PubMed:26515013 ]
LOTUS database [Link]

Showing NP-Card for kermesic acid (NP0266532)

MOL for NP0266532 (kermesic acid)

3D MOL for NP0266532 (kermesic acid)

3D SDF for NP0266532 (kermesic acid)

3D-SDF for NP0266532 (kermesic acid)

PDB for NP0266532 (kermesic acid)

3D PDB for NP0266532 (kermesic acid)

SMILES for NP0266532 (kermesic acid)

INCHI for NP0266532 (kermesic acid)

Structure for NP0266532 (kermesic acid)

3D Structure for NP0266532 (kermesic acid)