NP-MRD: Showing NP-Card for 2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal (NP0297736)

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Record Information

Version

2.0

Created at

2022-09-10 08:21:31 UTC

Updated at

2022-09-10 08:21:31 UTC

NP-MRD ID

NP0297736

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal

Description

2-(4A,7-dihydroxy-4,9-dioxo-2,3,4,4a,9,9a-hexahydro-1H-xanthen-3-yl)prop-2-enal belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. 2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal is found in Ganoderma applanatum. 2-(4A,7-dihydroxy-4,9-dioxo-2,3,4,4a,9,9a-hexahydro-1H-xanthen-3-yl)prop-2-enal is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.7802   -1.3344   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5565   -0.0757    0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2311    0.4070    1.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0568    1.5865    1.7854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6715    0.8299   -0.5520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2040    0.2356   -1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460   -0.5509   -1.7351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1479    0.2664   -1.0819 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4412   -0.4314   -1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7351   -1.3340   -1.9206 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430   -0.0524   -0.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7154   -0.5755   -0.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6311   -0.2000    0.8511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9127   -0.7151    0.8462 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886    0.6975    1.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091    1.2013    1.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0593    0.8507    0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7718    1.3787    0.9014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493    0.5465    0.3325 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3173   -0.6250    1.0444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5551    1.2681    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6558    2.2304    1.0543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4534   -1.9537    0.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3741   -1.8357   -0.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8775   -0.2202    1.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2195    1.7793   -0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0020   -0.3734   -2.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9872    1.0549   -2.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5730   -0.7421   -2.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0383   -1.5554   -1.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578    1.1939   -1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0013   -1.2894   -0.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6188   -0.2082    0.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0291    0.9687    2.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7032    1.9143    2.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170   -1.2202    0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  1
 19  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  5 21  1  0
 21 22  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 11 17  1  0
 21 19  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 20 36  1  0
  8 31  1  6
  7 29  1  0
  7 30  1  0
  6 27  1  0
  6 28  1  0
  5 26  1  6
  1 23  1  0
  1 24  1  0
  3 25  1  0
 12 32  1  0
M  END


  Mrv1533004241500032D          

 22 24  0  0  0  0            999 V2000
   -2.1434   -1.2375    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
   -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
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   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
    1.4289   -3.3000    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
    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
    2.8579   -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
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   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
    2.1434   -3.7125    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
    0.7145   -0.4125    0.0000 O   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
  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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  2  0  0  0  0
  9 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  2  0  0  0  0
  2 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0297736

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2OC3(O)C(CCC(C(=C)C=O)C3=O)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c1-8(7-17)10-3-4-12-14(19)11-6-9(18)2-5-13(11)22-16(12,21)15(10)20/h2,5-7,10,12,18,21H,1,3-4H2

> <INCHI_KEY>
OWPIQJAXQUDFDL-UHFFFAOYSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.282

> <EXACT_MASS>
302.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.46395322823786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4a,7-dihydroxy-4,9-dioxo-2,3,4,4a,9,9a-hexahydro-1H-xanthen-3-yl)prop-2-enal

> <ALOGPS_LOGP>
1.64

> <JCHEM_LOGP>
1.7298695990000001

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.679198644771246

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.012970422864619

> <JCHEM_PKA_STRONGEST_BASIC>
-4.758252068522917

> <JCHEM_POLAR_SURFACE_AREA>
100.89999999999998

> <JCHEM_REFRACTIVITY>
75.6612

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal

> <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  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667  -3.080   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  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   17                                             
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   12    7   18                                                  
CONECT   18   17                                                            
CONECT   19    9   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    5   22                                                  
CONECT   22   21    2                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₆

Average Mass

302.2820 Da

Monoisotopic Mass

302.07904 Da

IUPAC Name

2-(4a,7-dihydroxy-4,9-dioxo-2,3,4,4a,9,9a-hexahydro-1H-xanthen-3-yl)prop-2-enal

Traditional Name

2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal

CAS Registry Number

Not Available

SMILES

OC1=CC=C2OC3(O)C(CCC(C(=C)C=O)C3=O)C(=O)C2=C1

InChI Identifier

InChI=1S/C16H14O6/c1-8(7-17)10-3-4-12-14(19)11-6-9(18)2-5-13(11)22-16(12,21)15(10)20/h2,5-7,10,12,18,21H,1,3-4H2

InChI Key

OWPIQJAXQUDFDL-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

Species Name	Source	Reference
Ganoderma applanatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Alpha,beta-unsaturated aldehyde
Enal
Cyclic alcohol
Ketone
Hemiacetal
Oxacycle
Aldehyde
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	1.64	ALOGPS
logP	1.73	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.01	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.66 m³·mol⁻¹	ChemAxon
Polarizability	29.46 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal (NP0297736)

MOL for NP0297736 (2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal)

3D MOL for NP0297736 (2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal)

3D SDF for NP0297736 (2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal)

3D-SDF for NP0297736 (2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal)

PDB for NP0297736 (2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal)

3D PDB for NP0297736 (2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal)

SMILES for NP0297736 (2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal)

INCHI for NP0297736 (2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal)

Structure for NP0297736 (2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal)

3D Structure for NP0297736 (2-(4a,7-dihydroxy-4,9-dioxo-1,2,3,9a-tetrahydroxanthen-3-yl)prop-2-enal)