NP-MRD: Showing NP-Card for Citrinin (NP0046752)

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Record Information

Version

2.0

Created at

2022-03-17 20:28:58 UTC

Updated at

2024-09-03 04:19:15 UTC

NP-MRD ID

NP0046752

Natural Product DOI

https://doi.org/10.57994/1688

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Citrinin

Description

Citrinin is found in Aspergillus carneus, Crotalaria crispata, Guanomyces polythrix, Microsporum sp., Monascus purpureus, Monascus ruber, Monascus sp., Penicillium citrinum, Penicillium corylophilum, Penicillium notatum B-52, Penicillium odoratum, Penicillium purpurogenum G59, Penicillium simplicissimum, Penicillium sp. GO-7, Penicillium ultimum and Penicillium viridicatum. Citrinin was first documented in 2024 (PMID: 38286315).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241220462D          

 18 19  0  0  1  0            999 V2000
   -1.4289   -1.6500    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 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   -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 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
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  5 12  2  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
  4 15  1  0  0  0  0
 15 16  1  6  0  0  0
 14 17  1  1  0  0  0
  3 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046752

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1OC=C2C(=O)C(=C(O)O)C(=O)C(C)=C2[C@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,16-17H,1-3H3/t5-,7-/m0/s1

> <INCHI_KEY>
JLWQFKMKUKQXMW-FSPLSTOPSA-N

> <FORMULA>
C13H14O5

> <MOLECULAR_WEIGHT>
250.2473

> <EXACT_MASS>
250.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
24.527412353828936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4R)-7-(dihydroxymethylidene)-3,4,5-trimethyl-4,6,7,8-tetrahydro-3H-2-benzopyran-6,8-dione

> <ALOGPS_LOGP>
1.04

> <JCHEM_LOGP>
1.8783604353333334

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.9737405983562

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.157429850087401

> <JCHEM_PKA_STRONGEST_BASIC>
-4.796992086854245

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
74.57269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R)-7-(dihydroxymethylidene)-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-6,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14    4   16                                                  
CONECT   16   15                                                            
CONECT   17   14                                                            
CONECT   18    3                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₄O₅

Average Mass

250.2473 Da

Monoisotopic Mass

250.08412 Da

IUPAC Name

(3S,4R)-7-(dihydroxymethylidene)-3,4,5-trimethyl-4,6,7,8-tetrahydro-3H-2-benzopyran-6,8-dione

Traditional Name

(3S,4R)-7-(dihydroxymethylidene)-3,4,5-trimethyl-3,4-dihydro-2-benzopyran-6,8-dione

CAS Registry Number

642-15-9

SMILES

C[C@@H]1OC=C2C(=O)C(=C(O)O)C(=O)C(C)=C2[C@H]1C

InChI Identifier

InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,16-17H,1-3H3/t5-,7-/m0/s1

InChI Key

JLWQFKMKUKQXMW-FSPLSTOPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	545103346@qq.com	Nanjing University of Chinese Medicine	Ying Zhang	2024-05-02	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus carneus	Fungi	KNApSAcK
Crotalaria crispata	LOTUS Database	35616633
Guanomyces polythrix	Fungi	KNApSAcK
Hordeum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Microsporum sp.	Fungi	KNApSAcK
Monascus purpureus	Fungi	KNApSAcK
Monascus ruber	Fungi	KNApSAcK
Monascus sp.	Fungi	KNApSAcK
Penicillium citrinum	Fungi	KNApSAcK
Penicillium citrinum ZY-2		Not Available
Penicillium corylophilum	Fungi	KNApSAcK
Penicillium notatum B-52	Fungi	KNApSAcK
Penicillium odoratum	Fungi	KNApSAcK
Penicillium purpurogenum G59	Fungi	KNApSAcK
Penicillium simplicissimum	LOTUS Database	35616633
Penicillium sp. GO-7	Fungi	KNApSAcK
Penicillium ultimum	Fungi	KNApSAcK
Penicillium viridicatum	Fungi	KNApSAcK
Triticum aestivum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
O-quinomethane
Quinomethane
Cyclohexenone
Vinylogous acid
Vinylogous ester
Ketene acetal or derivatives
Ketone
Cyclic ketone
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.04	ALOGPS
logP	1.88	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	-1.2	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	74.57 m³·mol⁻¹	ChemAxon
Polarizability	24.53 Å³	ChemAxon
Number of Rings	2	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

FDB005766

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Citrinin

METLIN ID

Not Available

PubChem Compound

10611

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Citrinin (NP0046752)

MOL for NP0046752 (Citrinin)

3D MOL for NP0046752 (Citrinin)

3D SDF for NP0046752 (Citrinin)

3D-SDF for NP0046752 (Citrinin)

PDB for NP0046752 (Citrinin)

3D PDB for NP0046752 (Citrinin)

SMILES for NP0046752 (Citrinin)

INCHI for NP0046752 (Citrinin)

Structure for NP0046752 (Citrinin)

3D Structure for NP0046752 (Citrinin)