NP-MRD: Showing NP-Card for BL IV (NP0048047)

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Record Information

Version

2.0

Created at

2022-03-17 20:50:14 UTC

Updated at

2022-03-17 20:50:14 UTC

NP-MRD ID

NP0048047

Secondary Accession Numbers

None

Natural Product Identification

Common Name

BL IV

Description

Prexanthoperol, also known as hypargenin C, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Prexanthoperol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Prexanthoperol has been detected, but not quantified in, fruits. BL IV is found in Boletopsis leucomelas. This could make prexanthoperol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308012D          

 34 37  0  0  0  0            999 V2000
   -0.6867   -2.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636    2.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834   -0.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1544    1.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9614    1.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2585    0.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347   -1.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7566    2.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5134    1.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723   -1.7698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017    3.3795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863   -2.1129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3204    1.2701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    0.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    1.5105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 10  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  3  1  0  0  0  0
 13  4  2  0  0  0  0
 13  5  1  0  0  0  0
 14  6  2  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16  8  2  0  0  0  0
 17  9  2  0  0  0  0
 17 16  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  2  0  0  0  0
 19 13  1  0  0  0  0
 20 15  1  0  0  0  0
 21 19  2  0  0  0  0
 22 19  1  0  0  0  0
 23 20  2  0  0  0  0
 23 21  1  0  0  0  0
 24 20  1  0  0  0  0
 24 22  2  0  0  0  0
 25 10  2  0  0  0  0
 26 11  2  0  0  0  0
 27 12  2  0  0  0  0
 28 14  1  0  0  0  0
 29 16  1  0  0  0  0
 30 17  1  0  0  0  0
 31 10  1  0  0  0  0
 31 21  1  0  0  0  0
 32 11  1  0  0  0  0
 32 22  1  0  0  0  0
 33 12  1  0  0  0  0
 33 23  1  0  0  0  0
 34 18  1  0  0  0  0
 34 24  1  0  0  0  0
M  END


  Mrv0541 05061308012D          

 34 37  0  0  0  0            999 V2000
   -0.6867   -2.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636    2.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834   -0.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1544    1.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9614    1.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2585    0.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347   -1.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7566    2.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5134    1.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723   -1.7698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017    3.3795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863   -2.1129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3204    1.2701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    0.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    1.5105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 10  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  3  1  0  0  0  0
 13  4  2  0  0  0  0
 13  5  1  0  0  0  0
 14  6  2  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16  8  2  0  0  0  0
 17  9  2  0  0  0  0
 17 16  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  2  0  0  0  0
 19 13  1  0  0  0  0
 20 15  1  0  0  0  0
 21 19  2  0  0  0  0
 22 19  1  0  0  0  0
 23 20  2  0  0  0  0
 23 21  1  0  0  0  0
 24 20  1  0  0  0  0
 24 22  2  0  0  0  0
 25 10  2  0  0  0  0
 26 11  2  0  0  0  0
 27 12  2  0  0  0  0
 28 14  1  0  0  0  0
 29 16  1  0  0  0  0
 30 17  1  0  0  0  0
 31 10  1  0  0  0  0
 31 21  1  0  0  0  0
 32 11  1  0  0  0  0
 32 22  1  0  0  0  0
 33 12  1  0  0  0  0
 33 23  1  0  0  0  0
 34 18  1  0  0  0  0
 34 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048047

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1=C2OC3=C(C=C(O)C(O)=C3)C2=C(OC(C)=O)C(OC(C)=O)=C1C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H18O10/c1-10(25)31-21-19(13-4-6-14(28)7-5-13)22(32-11(2)26)24-20(23(21)33-12(3)27)15-8-16(29)17(30)9-18(15)34-24/h4-9,28-30H,1-3H3

> <INCHI_KEY>
DTOIFOOSMQSUBD-UHFFFAOYSA-N

> <FORMULA>
C24H18O10

> <MOLECULAR_WEIGHT>
466.3937

> <EXACT_MASS>
466.089996796

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
46.01780899620029

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,6-bis(acetyloxy)-11,12-dihydroxy-5-(4-hydroxyphenyl)-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2,4,6,10,12-hexaen-3-yl acetate

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
2.7095594169999995

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.45225161233461

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.463213117791172

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7068432074698427

> <JCHEM_POLAR_SURFACE_AREA>
152.73000000000002

> <JCHEM_REFRACTIVITY>
115.70289999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,6-bis(acetyloxy)-11,12-dihydroxy-5-(4-hydroxyphenyl)-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2,4,6,10,12-hexaen-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.282  -4.128   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.919   4.523   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.822  -1.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.155   2.875   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.709   0.266   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.661   3.195   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.216   0.586   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.411  -0.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.362   2.235   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.251  -2.983   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.412   4.844   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.792  -2.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.679   1.410   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.692   2.051   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.917  -0.374   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.393   1.090   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.173   1.090   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.255  -3.304   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.937   6.308   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.268  -3.944   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -6.198   2.371   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       7.947  -1.519   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.899   1.410   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.727  -1.519   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.382   3.699   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.285  -2.159   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       3.610   2.820   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4    6   13                                                       
CONECT    5    7   13                                                       
CONECT    6    4   14                                                       
CONECT    7    5   14                                                       
CONECT    8   15   16                                                       
CONECT    9   17   18                                                       
CONECT   10    1   25   31                                                  
CONECT   11    2   26   32                                                  
CONECT   12    3   27   33                                                  
CONECT   13    4    5   19                                                  
CONECT   14    6    7   28                                                  
CONECT   15    8   18   20                                                  
CONECT   16    8   17   29                                                  
CONECT   17    9   16   30                                                  
CONECT   18    9   15   34                                                  
CONECT   19   13   21   22                                                  
CONECT   20   15   23   24                                                  
CONECT   21   19   23   31                                                  
CONECT   22   19   24   32                                                  
CONECT   23   20   21   33                                                  
CONECT   24   20   22   34                                                  
CONECT   25   10                                                            
CONECT   26   11                                                            
CONECT   27   12                                                            
CONECT   28   14                                                            
CONECT   29   16                                                            
CONECT   30   17                                                            
CONECT   31   10   21                                                       
CONECT   32   11   22                                                       
CONECT   33   12   23                                                       
CONECT   34   18   24                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Hypargenin C	HMDB
Cibacron blue	HMDB
Cibacron blue 3ga	HMDB
Cibacron blue F 3ga	HMDB
Reactive blue 2	HMDB
3,4-Bis(acetyloxy)-11,12-dihydroxy-5-(4-hydroxyphenyl)-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2,4,6,10,12-hexaen-6-yl acetic acid	Generator

Chemical Formula

C₂₄H₁₈O₁₀

Average Mass

466.3937 Da

Monoisotopic Mass

466.09000 Da

IUPAC Name

4,6-bis(acetyloxy)-11,12-dihydroxy-5-(4-hydroxyphenyl)-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2,4,6,10,12-hexaen-3-yl acetate

Traditional Name

4,6-bis(acetyloxy)-11,12-dihydroxy-5-(4-hydroxyphenyl)-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2,4,6,10,12-hexaen-3-yl acetate

CAS Registry Number

112209-53-7

SMILES

CC(=O)OC1=C2OC3=C(C=C(O)C(O)=C3)C2=C(OC(C)=O)C(OC(C)=O)=C1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C24H18O10/c1-10(25)31-21-19(13-4-6-14(28)7-5-13)22(32-11(2)26)24-20(23(21)33-12(3)27)15-8-16(29)17(30)9-18(15)34-24/h4-9,28-30H,1-3H3

InChI Key

DTOIFOOSMQSUBD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Boletopsis leucomelas	-	KNApSAcK
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Abietane diterpenoid
Diterpenoid
Hydrophenanthrene
Phenanthrene
Naphthoquinone
Tetralin
Naphthalene
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Ketone
Carbonyl group
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.96	ALOGPS
logP	2.71	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.46	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	152.73 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	115.7 m³·mol⁻¹	ChemAxon
Polarizability	46.02 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0034712

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014424

KNApSAcK ID

Not Available

Chemspider ID

546062

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

628742

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for BL IV (NP0048047)

MOL for NP0048047 (BL IV)

3D MOL for NP0048047 (BL IV)

3D SDF for NP0048047 (BL IV)

3D-SDF for NP0048047 (BL IV)

PDB for NP0048047 (BL IV)

3D PDB for NP0048047 (BL IV)

SMILES for NP0048047 (BL IV)

INCHI for NP0048047 (BL IV)

Structure for NP0048047 (BL IV)

3D Structure for NP0048047 (BL IV)