NP-MRD: Showing NP-Card for Fulvic acid (NP0076570)

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Record Information

Version

2.0

Created at

2022-04-28 21:45:45 UTC

Updated at

2022-04-28 21:45:45 UTC

NP-MRD ID

NP0076570

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fulvic acid

Description

(R)-Fulvic acid, also known as (R)-fulvate, belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety. Fulvic acid is found in Cercospora beticola, Penicillium restrictum and Penicillium striatisporum. Fulvic acid was first documented in 2022 (PMID: 35489570). Based on a literature review a small amount of articles have been published on (R)-Fulvic acid (PMID: 35447213) (PMID: 35302348) (PMID: 35258211) (PMID: 35174701).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    4.9216   -0.6179   -0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5836   -0.0510    0.3082 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7050    0.5332    1.5662 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6129   -1.2076    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2230   -0.6727    0.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2090   -1.4683    0.3626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0327   -1.0994    0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233   -2.0345    0.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3384   -1.6252    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3405   -2.5869    0.3682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516   -0.3302   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9579    0.0598   -0.2092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6460    0.6526   -0.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0758    1.9893   -0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3611    2.9829   -0.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4740    2.2287   -0.6334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3494    0.2290   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3196    1.1278   -0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4656    2.3499   -0.4596 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    0.6409   -0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0864    1.6068   -0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2025    0.8938   -0.6102 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7587   -1.1374   -1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3091   -1.3046    0.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6553    0.2062   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0636    1.4482    1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6700   -1.6957    1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102   -1.9800   -0.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323   -3.0740    0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3114   -2.4232    0.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7415   -0.5426   -0.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9728    2.4291    0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8674    2.3825   -0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2373    2.0905    0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  5  1  0
  5 20  2  0
 20 21  1  0
 21 22  1  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 17 13  2  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
 13 11  1  0
 11 12  1  0
 11  9  2  0
  9 10  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
 22  2  1  0
  7 17  1  0
  6  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
 21 33  1  0
 21 34  1  0
 16 32  1  0
 12 31  1  0
 10 30  1  0
  8 29  1  0
M  END


  Mrv1652304282223452D          

 22 24  0  0  1  0            999 V2000
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7240    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1113    0.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  1  0  0  0
  4  8  1  6  0  0  0
  2  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
  1 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 10 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076570

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(O)CC2=C(CO1)C(=O)C1=C(C(O)=O)C(O)=C(O)C=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O8/c1-14(20)3-8-5(4-21-14)11(16)9-7(22-8)2-6(15)12(17)10(9)13(18)19/h2,15,17,20H,3-4H2,1H3,(H,18,19)/t14-/m1/s1

> <INCHI_KEY>
FCYKAQOGGFGCMD-CQSZACIVSA-N

> <FORMULA>
C14H12O8

> <MOLECULAR_WEIGHT>
308.242

> <EXACT_MASS>
308.053217346

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.537552213354303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-3,7,8-trihydroxy-3-methyl-10-oxo-1H,3H,4H,10H-pyrano[4,3-b]chromene-9-carboxylic acid

> <ALOGPS_LOGP>
0.85

> <JCHEM_LOGP>
0.9557203773333334

> <ALOGPS_LOGS>
-2.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.67544152086902

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2643934434930153

> <JCHEM_PKA_STRONGEST_BASIC>
-4.036418104746001

> <JCHEM_POLAR_SURFACE_AREA>
133.51999999999998

> <JCHEM_REFRACTIVITY>
72.9941

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3,7,8-trihydroxy-3-methyl-10-oxo-1H,4H-pyrano[4,3-b]chromene-9-carboxylic 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       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.818   2.846   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.541   1.594   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   12                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7    8                                             
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    2   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11    1   13                                                  
CONECT   13   12                                                            
CONECT   14   11   15   20                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   10                                                       
CONECT   18   16                                                            
CONECT   19   15                                                            
CONECT   20   14   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
(R)-Fulvate	Generator

Chemical Formula

C₁₄H₁₂O₈

Average Mass

308.2420 Da

Monoisotopic Mass

308.05322 Da

IUPAC Name

(3R)-3,7,8-trihydroxy-3-methyl-10-oxo-1H,3H,4H,10H-pyrano[4,3-b]chromene-9-carboxylic acid

Traditional Name

(3R)-3,7,8-trihydroxy-3-methyl-10-oxo-1H,4H-pyrano[4,3-b]chromene-9-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@]1(O)CC2=C(CO1)C(=O)C1=C(C(O)=O)C(O)=C(O)C=C1O2

InChI Identifier

InChI=1S/C14H12O8/c1-14(20)3-8-5(4-21-14)11(16)9-7(22-8)2-6(15)12(17)10(9)13(18)19/h2,15,17,20H,3-4H2,1H3,(H,18,19)/t14-/m1/s1

InChI Key

FCYKAQOGGFGCMD-CQSZACIVSA-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
Cercospora beticola	LOTUS Database	35616633
Penicillium restrictum	LOTUS Database	35616633
Penicillium striatisporum	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromones

Alternative Parents

Substituents

Chromone
Hydroxybenzoic acid
Salicylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Hemiacetal
Oxacycle
Polyol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.85	ALOGPS
logP	0.96	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	2.26	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.99 m³·mol⁻¹	ChemAxon
Polarizability	28.54 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

24732399

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

51382658

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lu K, Ping Q, Lu Q, Li Y: Understanding roles of humic substance and protein on iron phosphate transformation during anaerobic fermentation of waste activated sludge. Bioresour Technol. 2022 Jul;355:127242. doi: 10.1016/j.biortech.2022.127242. Epub 2022 Apr 28. [PubMed:35489570 ]
Wang Q, Huang Q, Wang J, Li H, Qin J, Li X, Gouda SG, Liu Y, Liu Q, Guo G, Khan MA, Su X, Lin L, Qin J, Lu W, Zhao Y, Hu S, Wang J: Ecological circular agriculture: A case study evaluating biogas slurry applied to rice in two soils. Chemosphere. 2022 Aug;301:134628. doi: 10.1016/j.chemosphere.2022.134628. Epub 2022 Apr 18. [PubMed:35447213 ]
Lei X, Lei Y, Guan J, Westerhoff P, Yang X: Kinetics and Transformations of Diverse Dissolved Organic Matter Fractions with Sulfate Radicals. Environ Sci Technol. 2022 Apr 5;56(7):4457-4466. doi: 10.1021/acs.est.1c08388. Epub 2022 Mar 18. [PubMed:35302348 ]
Song YL, Yu Y, Zheng L, Wang H, Zhu WF: [Adsorption of Fulvic Acid on Virgin and Aging Microplastics]. Huan Jing Ke Xue. 2022 Mar 8;43(3):1472-1480. doi: 10.13227/j.hjkx.202107034. [PubMed:35258211 ]
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Showing NP-Card for Fulvic acid (NP0076570)

MOL for NP0076570 (Fulvic acid)

3D MOL for NP0076570 (Fulvic acid)

3D SDF for NP0076570 (Fulvic acid)

3D-SDF for NP0076570 (Fulvic acid)

PDB for NP0076570 (Fulvic acid)

3D PDB for NP0076570 (Fulvic acid)

SMILES for NP0076570 (Fulvic acid)

INCHI for NP0076570 (Fulvic acid)

Structure for NP0076570 (Fulvic acid)

3D Structure for NP0076570 (Fulvic acid)