NP-MRD: Showing NP-Card for 1'S-2',3'-dihydroprotoapigenone (NP0351118)

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Record Information

Version

2.0

Created at

2025-06-04 00:45:15 UTC

Updated at

2025-06-04 04:00:29 UTC

NP-MRD ID

NP0351118

Natural Product DOI

https://doi.org/10.57994/4107

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1'S-2',3'-dihydroprotoapigenone

Description

1'S-2',3'-dihydroprotoapigenone was first documented in 2025 (PMID: 40437909).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03172303092D          

 21 23  0  0  1  0            999 V2000
   -1.4289    0.0000    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
   -0.7145   -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
    0.0000   -2.4750    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 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
    1.4289   -0.0000    0.0000 O   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 C   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1401   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4222    1.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7044    2.3257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9525    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6704    0.1433    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  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 10  1  6  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 14 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0351118

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C2C(=O)C=C(OC2=C1)[C@]1(O)CCC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O6/c16-8-1-3-15(20,4-2-8)13-7-11(19)14-10(18)5-9(17)6-12(14)21-13/h1,3,5-7,17-18,20H,2,4H2/t15-/m1/s1

> <INCHI_KEY>
RGJFSGDUSSUZRV-OAHLLOKOSA-N

> <FORMULA>
C15H12O6

> <MOLECULAR_WEIGHT>
288.255

> <EXACT_MASS>
288.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.366431077402233

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-[(1S)-1-hydroxy-4-oxocyclohex-2-en-1-yl]-4H-chromen-4-one

> <JCHEM_LOGP>
1.565065129

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.183203673882414

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.580427325120132

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6563436719811624

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
75.0972

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-[(1S)-1-hydroxy-4-oxocyclohex-2-en-1-yl]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAR-23         0                                  
HETATM    1  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.861  -1.447   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.872   2.627   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.388   2.894   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.915   4.341   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.378   1.715   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.851   0.267   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12                                                            
CONECT   14   10   15   16   21                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₆

Average Mass

288.2550 Da

Monoisotopic Mass

288.06339 Da

IUPAC Name

5,7-dihydroxy-2-[(1S)-1-hydroxy-4-oxocyclohex-2-en-1-yl]-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2-[(1S)-1-hydroxy-4-oxocyclohex-2-en-1-yl]chromen-4-one

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C2C(=O)C=C(OC2=C1)[C@]1(O)CCC(=O)C=C1

InChI Identifier

InChI=1S/C15H12O6/c16-8-1-3-15(20,4-2-8)13-7-11(19)14-10(18)5-9(17)6-12(14)21-13/h1,3,5-7,17-18,20H,2,4H2/t15-/m1/s1

InChI Key

RGJFSGDUSSUZRV-OAHLLOKOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	527972162@qq.com	hebei university of chinese medicine	jiankun yan	2025-06-04	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	527972162@qq.com	hebei university of chinese medicine	jiankun yan	2025-06-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	527972162@qq.com	hebei university of chinese medicine	jiankun yan	2025-06-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	527972162@qq.com	hebei university of chinese medicine	jiankun yan	2025-06-04	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	527972162@qq.com	hebei university of chinese medicine	jiankun yan	2025-06-04	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	527972162@qq.com	hebei university of chinese medicine	jiankun yan	2025-06-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	527972162@qq.com	hebei university of chinese medicine	jiankun yan	2025-06-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	527972162@qq.com	hebei university of chinese medicine	jiankun yan	2025-06-04	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Polytrichum commune		Not Available

Chemical Taxonomy

Classification

Not classified

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	1.57	ChemAxon
pKa (Strongest Acidic)	6.58	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.1 m³·mol⁻¹	ChemAxon
Polarizability	27.37 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

Dong JJ, Han DR, Cheng H, Shi XL, Ma DL, Yan JK, Duan XH: Two new protoflavonoids from Polytrichum commune and their cytotoxicity against human gastric cancer cells. Nat Prod Res. 2025 May 29:1-7. doi: 10.1080/14786419.2025.2512562. [PubMed:40437909 ]
DOI: 10.1080/14786419.2025.2512562
PMID: 40437909

Showing NP-Card for 1'S-2',3'-dihydroprotoapigenone (NP0351118)

MOL for NP0351118 (1'S-2',3'-dihydroprotoapigenone)

3D MOL for NP0351118 (1'S-2',3'-dihydroprotoapigenone)

3D SDF for NP0351118 (1'S-2',3'-dihydroprotoapigenone)

3D-SDF for NP0351118 (1'S-2',3'-dihydroprotoapigenone)

PDB for NP0351118 (1'S-2',3'-dihydroprotoapigenone)

3D PDB for NP0351118 (1'S-2',3'-dihydroprotoapigenone)

SMILES for NP0351118 (1'S-2',3'-dihydroprotoapigenone)

INCHI for NP0351118 (1'S-2',3'-dihydroprotoapigenone)

Structure for NP0351118 (1'S-2',3'-dihydroprotoapigenone)

3D Structure for NP0351118 (1'S-2',3'-dihydroprotoapigenone)