NP-MRD: Showing NP-Card for 9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one (NP0324491)

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Record Information

Version

2.0

Created at

2022-09-12 04:36:06 UTC

Updated at

2022-09-12 04:36:06 UTC

NP-MRD ID

NP0324491

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one

Description

9-(3-Chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-5-one belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-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. Based on a literature review very few articles have been published on 9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-5-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122206362D          

 32 35  0  0  0  0            999 V2000
    2.2221   -3.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -3.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7032   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433   -0.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732    0.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433    1.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7528    0.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1937    0.7021    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -3.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1124   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -3.3098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  4  5  1  0  0  0  0
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 31 32  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309122206362D          

 32 35  0  0  0  0            999 V2000
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    3.0323   -3.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3023   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724    0.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0324491

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1COC2=C(C)C=C3OC4=C(CC(O)C(C)(C)Cl)C=CC(O)=C4C(=O)C3=C2C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H27ClO6/c1-11(2)14-10-31-23-12(3)8-16-19(20(23)21(14)29)22(30)18-15(27)7-6-13(24(18)32-16)9-17(28)25(4,5)26/h6-8,14,17,21,27-29H,1,9-10H2,2-5H3

> <INCHI_KEY>
ZBWJGCYJNCJUFS-UHFFFAOYSA-N

> <FORMULA>
C25H27ClO6

> <MOLECULAR_WEIGHT>
458.94

> <EXACT_MASS>
458.1496163

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
48.46575270925521

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-5-one

> <JCHEM_LOGP>
4.648662675000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.398084816095931

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.67809377571874

> <JCHEM_PKA_STRONGEST_BASIC>
-3.334949613781892

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
122.669

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2H-1,10-dioxatetraphen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       4.148  -7.051   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.660  -6.760   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -7.924   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.660  -2.686   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.677  -0.940   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   0.224   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.189  -0.649   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.709  -1.522   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.734  -0.940   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.246  -0.649   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      17.254  -1.813   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      16.750   0.807   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.254   2.262   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.205   0.302   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0      15.295   1.311   0.000  0.00  0.00          Cl+0
HETATM   22  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.717  -6.760   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.197  -5.887   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.685  -6.178   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   31                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   26                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   14   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   13   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   11   30                                                  
CONECT   30   29    7   31                                                  
CONECT   31   30    4   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₇ClO₆

Average Mass

458.9400 Da

Monoisotopic Mass

458.14962 Da

IUPAC Name

9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-5-one

Traditional Name

9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2H-1,10-dioxatetraphen-5-one

CAS Registry Number

Not Available

SMILES

CC(=C)C1COC2=C(C)C=C3OC4=C(CC(O)C(C)(C)Cl)C=CC(O)=C4C(=O)C3=C2C1O

InChI Identifier

InChI=1S/C25H27ClO6/c1-11(2)14-10-31-23-12(3)8-16-19(20(23)21(14)29)22(30)18-15(27)7-6-13(24(18)32-16)9-17(28)25(4,5)26/h6-8,14,17,21,27-29H,1,9-10H2,2-5H3

InChI Key

ZBWJGCYJNCJUFS-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-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

4-prenylated xanthones

Alternative Parents

Substituents

4-prenylated xanthone
Pyranoxanthone
Chromone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Chlorohydrin
Halohydrin
Oxacycle
Ether
Hydrocarbon derivative
Organohalogen compound
Organochloride
Organooxygen compound
Alcohol
Alkyl chloride
Alkyl halide
Organic oxygen compound
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	4.65	ChemAxon
pKa (Strongest Acidic)	8.68	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.67 m³·mol⁻¹	ChemAxon
Polarizability	48.47 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	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

75995409

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one (NP0324491)

MOL for NP0324491 (9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

3D MOL for NP0324491 (9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

3D SDF for NP0324491 (9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

3D-SDF for NP0324491 (9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

PDB for NP0324491 (9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

3D PDB for NP0324491 (9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

SMILES for NP0324491 (9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

INCHI for NP0324491 (9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

Structure for NP0324491 (9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

3D Structure for NP0324491 (9-(3-chloro-2-hydroxy-3-methylbutyl)-4,6-dihydroxy-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)