NP-MRD: Showing NP-Card for 4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one (NP0199904)

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Record Information

Version

2.0

Created at

2022-09-04 18:38:09 UTC

Updated at

2022-09-04 18:38:09 UTC

NP-MRD ID

NP0199904

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one

Description

Chaetochromin D belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. 4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one is found in Collariella gracilis. 4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one was first documented in 1993 (PMID: 23606174). Based on a literature review very few articles have been published on Chaetochromin D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042220382D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042220382D          

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 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  8 20  2  0  0  0  0
 14 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  2  0  0  0  0
  7 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  6 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  4 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
  2 39  2  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0199904

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1OC2=CC3=C(C(O)=CC(O)=C3C(O)=C2C(=O)[C@H]1C)C1=C2C=C3OC(C)=C(C)C(O)=C3C(O)=C2C(O)=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O10/c1-9-11(3)39-19-5-13-21(15(31)7-17(33)23(13)29(37)25(19)27(9)35)22-14-6-20-26(28(36)10(2)12(4)40-20)30(38)24(14)18(34)8-16(22)32/h5-9,11,31,33-34,36-38H,1-4H3/t9-,11-/m0/s1

> <INCHI_KEY>
BDIZPQDFMHMOFZ-ONGXEEELSA-N

> <FORMULA>
C30H24O10

> <MOLECULAR_WEIGHT>
544.512

> <EXACT_MASS>
544.136946973

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
55.876189456906786

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5,6-trihydroxy-2,3-dimethyl-9-[(2S,3S)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2H,3H,4H-naphtho[2,3-b]pyran-9-yl]-8H-cyclohexa[g]chromen-8-one

> <JCHEM_LOGP>
3.1034746869999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.664980232202384

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.998257458396411

> <JCHEM_PKA_STRONGEST_BASIC>
2.625929756104416

> <JCHEM_POLAR_SURFACE_AREA>
173.97999999999996

> <JCHEM_REFRACTIVITY>
150.2582

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4,5,6-trihydroxy-2,3-dimethyl-9-[(2S,3S)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2H,3H-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000  10.780   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.000   0.000   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   36                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8   28                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   26                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19    8   14                                                  
CONECT   21   18   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26                                                            
CONECT   28    7   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    6   34                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    4   37                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    2   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
Chaetochromin b	MeSH
Chaetochromin, stereoisomer	MeSH
Chaetochromin	MeSH
Chaetochromin a	MeSH

Chemical Formula

C₃₀H₂₄O₁₀

Average Mass

544.5120 Da

Monoisotopic Mass

544.13695 Da

IUPAC Name

4,5,6-trihydroxy-2,3-dimethyl-9-[(2S,3S)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2H,3H,4H-naphtho[2,3-b]pyran-9-yl]-8H-cyclohexa[g]chromen-8-one

Traditional Name

4,5,6-trihydroxy-2,3-dimethyl-9-[(2S,3S)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2H,3H-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1OC2=CC3=C(C(O)=CC(O)=C3C(O)=C2C(=O)[C@H]1C)C1=C2C=C3OC(C)=C(C)C(O)=C3C(O)=C2C(O)=CC1=O

InChI Identifier

InChI=1S/C30H24O10/c1-9-11(3)39-19-5-13-21(15(31)7-17(33)23(13)29(37)25(19)27(9)35)22-14-6-20-26(28(36)10(2)12(4)40-20)30(38)24(14)18(34)8-16(22)32/h5-9,11,31,33-34,36-38H,1-4H3/t9-,11-/m0/s1

InChI Key

BDIZPQDFMHMOFZ-ONGXEEELSA-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
Achaetomiella gracilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Benzochromone
Biphenol
1-naphthol
2-naphthol
Chromone
1-benzopyran
Naphthalene
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Cyclic ketone
Ketone
Oxacycle
Polyol
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	3.1	ChemAxon
pKa (Strongest Acidic)	7	ChemAxon
pKa (Strongest Basic)	2.63	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	150.26 m³·mol⁻¹	ChemAxon
Polarizability	55.88 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

136086707

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mori S, Kawai K, Nozawa Y, Koyama K, Natori S: The impairing effects of chaetochromin D on mitochondrial respiration and structure. Mycotoxin Res. 1993 Sep;9(2):85-93. doi: 10.1007/BF03192239. [PubMed:23606174 ]
LOTUS database [Link]

Showing NP-Card for 4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one (NP0199904)

MOL for NP0199904 (4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one)

3D MOL for NP0199904 (4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one)

3D SDF for NP0199904 (4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one)

3D-SDF for NP0199904 (4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one)

PDB for NP0199904 (4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one)

3D PDB for NP0199904 (4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one)

SMILES for NP0199904 (4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one)

INCHI for NP0199904 (4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one)

Structure for NP0199904 (4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one)

3D Structure for NP0199904 (4,5,6-trihydroxy-2,3-dimethyl-9-[(2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one)