NP-MRD: Showing NP-Card for 4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone (NP0336917)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 08:25:16 UTC

Updated at

2024-09-11 08:25:16 UTC

NP-MRD ID

NP0336917

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone

Description

4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone belongs to the class of organic compounds known as 2-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 2-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. 4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone has been detected, but not quantified in, fruits and herbs and spices. This could make 4-(1,1-dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061312352D          

 29 31  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   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
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    2.1434    2.0625    0.0000 O   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
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  8  7  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 19 16  1  0  0  0  0
 20 18  2  0  0  0  0
 21 13  2  0  0  0  0
 21 20  1  0  0  0  0
 22 16  2  0  0  0  0
 22 17  1  0  0  0  0
 23  4  1  0  0  0  0
 23  5  1  0  0  0  0
 23  6  1  0  0  0  0
 23 17  1  0  0  0  0
 24 14  1  0  0  0  0
 25 15  1  0  0  0  0
 26 18  1  0  0  0  0
 27 19  2  0  0  0  0
 28 20  1  0  0  0  0
 29 21  1  0  0  0  0
 29 22  1  0  0  0  0
M  END


  Mrv0541 05061312352D          

 29 31  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   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
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    2.1434    2.0625    0.0000 O   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
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  8  7  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 19 16  1  0  0  0  0
 20 18  2  0  0  0  0
 21 13  2  0  0  0  0
 21 20  1  0  0  0  0
 22 16  2  0  0  0  0
 22 17  1  0  0  0  0
 23  4  1  0  0  0  0
 23  5  1  0  0  0  0
 23  6  1  0  0  0  0
 23 17  1  0  0  0  0
 24 14  1  0  0  0  0
 25 15  1  0  0  0  0
 26 18  1  0  0  0  0
 27 19  2  0  0  0  0
 28 20  1  0  0  0  0
 29 21  1  0  0  0  0
 29 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336917

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC2=C(OC3=C(C(O)=CC(O)=C3C(C)(C)C=C)C2=O)C(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O6/c1-6-23(4,5)17-15(25)10-14(24)16-19(27)13-9-12(8-7-11(2)3)18(26)20(28)21(13)29-22(16)17/h6-7,9-10,24-26,28H,1,8H2,2-5H3

> <INCHI_KEY>
BPIPRLPHPUGIIF-UHFFFAOYSA-N

> <FORMULA>
C23H24O6

> <MOLECULAR_WEIGHT>
396.4331

> <EXACT_MASS>
396.1572885

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
42.787746342824654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3,5,6-tetrahydroxy-7-(3-methylbut-2-en-1-yl)-4-(2-methylbut-3-en-2-yl)-9H-xanthen-9-one

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
5.809582882333332

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.691488639175388

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.080986023427629

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1815680718323565

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
112.29369999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,5,6-tetrahydroxy-7-(3-methylbut-2-en-1-yl)-4-(2-methylbut-3-en-2-yl)xanthen-9-one

> <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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.671   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.541  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.461  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+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   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4   23                                                            
CONECT    5   23                                                            
CONECT    6    1   23                                                       
CONECT    7    8   11                                                       
CONECT    8    7   12                                                       
CONECT    9   12   13                                                       
CONECT   10   14   15                                                       
CONECT   11    2    3    7                                                  
CONECT   12    8    9   18                                                  
CONECT   13    9   19   21                                                  
CONECT   14   10   16   24                                                  
CONECT   15   10   17   25                                                  
CONECT   16   14   19   22                                                  
CONECT   17   15   22   23                                                  
CONECT   18   12   20   26                                                  
CONECT   19   13   16   27                                                  
CONECT   20   18   21   28                                                  
CONECT   21   13   20   29                                                  
CONECT   22   16   17   29                                                  
CONECT   23    4    5    6   17                                             
CONECT   24   14                                                            
CONECT   25   15                                                            
CONECT   26   18                                                            
CONECT   27   19                                                            
CONECT   28   20                                                            
CONECT   29   21   22                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Value	Source
4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-(3-methyl-2-butenyl)-9H-xanthen-9-one, 9ci	HMDB

Chemical Formula

C₂₃H₂₄O₆

Average Mass

396.4331 Da

Monoisotopic Mass

396.15729 Da

IUPAC Name

1,3,5,6-tetrahydroxy-7-(3-methylbut-2-en-1-yl)-4-(2-methylbut-3-en-2-yl)-9H-xanthen-9-one

Traditional Name

1,3,5,6-tetrahydroxy-7-(3-methylbut-2-en-1-yl)-4-(2-methylbut-3-en-2-yl)xanthen-9-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=CC2=C(OC3=C(C(O)=CC(O)=C3C(C)(C)C=C)C2=O)C(O)=C1O

InChI Identifier

InChI=1S/C23H24O6/c1-6-23(4,5)17-15(25)10-14(24)16-19(27)13-9-12(8-7-11(2)3)18(26)20(28)21(13)29-22(16)17/h6-7,9-10,24-26,28H,1,8H2,2-5H3

InChI Key

BPIPRLPHPUGIIF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 2-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2-prenylated xanthones

Alternative Parents

Substituents

2-prenylated xanthone
Chromone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Polyol
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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	4.26	ALOGPS
logP	5.81	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.08	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.29 m³·mol⁻¹	ChemAxon
Polarizability	42.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041338

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021261

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

131753111

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone (NP0336917)

MOL for NP0336917 (4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone)

3D MOL for NP0336917 (4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone)

3D SDF for NP0336917 (4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone)

3D-SDF for NP0336917 (4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone)

PDB for NP0336917 (4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone)

3D PDB for NP0336917 (4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone)

SMILES for NP0336917 (4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone)

INCHI for NP0336917 (4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone)

Structure for NP0336917 (4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone)

3D Structure for NP0336917 (4-(1,1-Dimethyl-2-propenyl)-1,3,5,6-tetrahydroxy-7-prenylxanthone)