NP-MRD: Showing NP-Card for (2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one (NP0163602)

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Record Information

Version

2.0

Created at

2022-09-02 22:17:40 UTC

Updated at

2022-09-02 22:17:40 UTC

NP-MRD ID

NP0163602

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one

Description

ISOCOCHLIOQUINONE C 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. (2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one is found in Pyrenophora dematioidea. Based on a literature review very few articles have been published on ISOCOCHLIOQUINONE C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032200172D          

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M  END

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  Mrv1652309032200172D          

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  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 18 33  1  0  0  0  0
 33 34  1  1  0  0  0
 13 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0163602

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)[C@@H](C)C1=CC(O)=C2C(=O)[C@H]3[C@@](C)(CC[C@H]4O[C@H](CC[C@]34C)C(C)(C)O)OC2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O7/c1-8-14(2)21(30)15(3)16-13-17(29)20-23(32)25-27(6)11-9-18(26(4,5)33)34-19(27)10-12-28(25,7)35-24(20)22(16)31/h13-15,18-19,25,29,31,33H,8-12H2,1-7H3/t14-,15-,18+,19+,25+,27-,28+/m0/s1

> <INCHI_KEY>
NZUVNIFDHVYNAE-AXSAHRJFSA-N

> <FORMULA>
C28H40O7

> <MOLECULAR_WEIGHT>
488.621

> <EXACT_MASS>
488.277403628

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.7673062731827

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4aR,4bR,10aR,12aR)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2S,4S)-4-methyl-3-oxohexan-2-yl]-2,3,4,4a,4b,5,10a,11,12,12a-decahydro-1,10-dioxatetraphen-5-one

> <ALOGPS_LOGP>
4.51

> <JCHEM_LOGP>
5.333621380000001

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.033519834160687

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.0516569621461

> <JCHEM_PKA_STRONGEST_BASIC>
-3.09355671023493

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
132.39530000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4aR,4bR,10aR,12aR)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2S,4S)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2H-1,10-dioxatetraphen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.063  -2.704   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.449  -2.995   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.457  -1.831   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.953  -0.376   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.969  -2.122   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.473  -3.577   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.978  -0.958   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.473   0.497   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.490  -1.249   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.994  -2.704   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.506  -2.995   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.010  -4.450   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.514  -1.831   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.010  -0.376   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.498  -0.085   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.994   1.370   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.018   0.788   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.531   0.497   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.027   1.952   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.539   1.661   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.051   1.370   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.555  -0.085   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      16.067  -0.376   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      16.571  -1.831   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.084  -2.122   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.596  -2.413   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.793  -3.634   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.375  -0.610   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      15.563  -2.995   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.051  -2.704   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.547  -1.249   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.539  -2.413   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.035  -0.958   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.027  -2.122   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      11.531  -3.577   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   34                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14    9   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   20   33                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29   24   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   22   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   18   34                                                  
CONECT   34   33   13   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀O₇

Average Mass

488.6210 Da

Monoisotopic Mass

488.27740 Da

IUPAC Name

(2R,4aR,4bR,10aR,12aR)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2S,4S)-4-methyl-3-oxohexan-2-yl]-2,3,4,4a,4b,5,10a,11,12,12a-decahydro-1,10-dioxatetraphen-5-one

Traditional Name

(2R,4aR,4bR,10aR,12aR)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2S,4S)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2H-1,10-dioxatetraphen-5-one

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)[C@@H](C)C1=CC(O)=C2C(=O)[C@H]3[C@@](C)(CC[C@H]4O[C@H](CC[C@]34C)C(C)(C)O)OC2=C1O

InChI Identifier

InChI=1S/C28H40O7/c1-8-14(2)21(30)15(3)16-13-17(29)20-23(32)25-27(6)11-9-18(26(4,5)33)34-19(27)10-12-28(25,7)35-24(20)22(16)31/h13-15,18-19,25,29,31,33H,8-12H2,1-7H3/t14-,15-,18+,19+,25+,27-,28+/m0/s1

InChI Key

NZUVNIFDHVYNAE-AXSAHRJFSA-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
Helminthosporium dematioideum	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
Prenylbenzoquinol
Chromone
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Oxane
Benzenoid
Tertiary alcohol
Vinylogous acid
Ketone
Ether
Dialkyl ether
Oxacycle
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.51	ALOGPS
logP	5.33	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.05	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	132.4 m³·mol⁻¹	ChemAxon
Polarizability	54.77 Å³	ChemAxon
Number of Rings	4	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00045326

Chemspider ID

31111161

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76309270

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one (NP0163602)

MOL for NP0163602 ((2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one)

3D MOL for NP0163602 ((2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one)

3D SDF for NP0163602 ((2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one)

3D-SDF for NP0163602 ((2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one)

PDB for NP0163602 ((2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one)

3D PDB for NP0163602 ((2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one)

SMILES for NP0163602 ((2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one)

INCHI for NP0163602 ((2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one)

Structure for NP0163602 ((2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one)

3D Structure for NP0163602 ((2r,4ar,4br,10ar,12ar)-6,9-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-3,4,4b,11,12,12a-hexahydro-2h-1,10-dioxatetraphen-5-one)