NP-MRD: Showing NP-Card for (3s,4r)-4,6-dihydroxy-9-[(2s)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one (NP0295646)

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Record Information

Version

2.0

Created at

2022-09-10 04:44:47 UTC

Updated at

2022-09-10 04:44:48 UTC

NP-MRD ID

NP0295646

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Tajixanthone methanoate 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. (3s,4r)-4,6-dihydroxy-9-[(2s)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one is found in Aspergillus rugulosus and Aspergillus stellatus. (3s,4r)-4,6-dihydroxy-9-[(2s)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one was first documented in 2006 (PMID: 16526278). Based on a literature review a small amount of articles have been published on tajixanthone methanoate (PMID: 19627125) (PMID: 30294975).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102206442D          

 33 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102206442D          

 33 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0295646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(C)(C)[C@@H](O)CC1=C2OC3=CC(C)=C4OC[C@@H]([C@@H](O)C4=C3C(=O)C2=C(O)C=C1)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O7/c1-12(2)15-11-32-24-13(3)9-17-20(21(24)22(15)29)23(30)19-16(27)8-7-14(25(19)33-17)10-18(28)26(4,5)31-6/h7-9,15,18,22,27-29H,1,10-11H2,2-6H3/t15-,18+,22-/m1/s1

> <INCHI_KEY>
QWNQVPWHVUVFIF-FXCLAUTBSA-N

> <FORMULA>
C26H30O7

> <MOLECULAR_WEIGHT>
454.519

> <EXACT_MASS>
454.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
49.125540477275564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.937197322666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.421535015288676

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.6734533712467

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3070713969956405

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
124.36919999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-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      13.726   0.224   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.213  -0.067   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.230   1.680   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.685   1.176   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.774   2.184   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.734   3.135   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.726   4.299   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.717  -6.760   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.197  -5.887   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM   33  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   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   31                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   27                                                  
CONECT   14   13   15   23                                                  
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   22                                                       
CONECT   22   21                                                            
CONECT   23   14   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   13   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   11   31                                                  
CONECT   31   30    7   32                                                  
CONECT   32   31    4   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
Tajixanthone methanoic acid	Generator

Chemical Formula

C₂₆H₃₀O₇

Average Mass

454.5190 Da

Monoisotopic Mass

454.19915 Da

IUPAC Name

(3S,4R)-4,6-dihydroxy-9-[(2S)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-5-one

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC(C)(C)[C@@H](O)CC1=C2OC3=CC(C)=C4OC[C@@H]([C@@H](O)C4=C3C(=O)C2=C(O)C=C1)C(C)=C

InChI Identifier

InChI=1S/C26H30O7/c1-12(2)15-11-32-24-13(3)9-17-20(21(24)22(15)29)23(30)19-16(27)8-7-14(25(19)33-17)10-18(28)26(4,5)31-6/h7-9,15,18,22,27-29H,1,10-11H2,2-6H3/t15-,18+,22-/m1/s1

InChI Key

QWNQVPWHVUVFIF-FXCLAUTBSA-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
Aspergillus rugulosus	LOTUS Database	35616633
Aspergillus stellatus	LOTUS Database	35616633

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
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Organic oxygen compound
Alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	3.94	ChemAxon
pKa (Strongest Acidic)	8.67	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.37 m³·mol⁻¹	ChemAxon
Polarizability	49.13 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

24659752

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46883486

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Moosophon P, Kanokmedhakul S, Kanokmedhakul K, Soytong K: Prenylxanthones and a bicyclo[3.3.1]nona-2,6-diene derivative from the fungus Emericella rugulosa. J Nat Prod. 2009 Aug;72(8):1442-6. doi: 10.1021/np800805f. [PubMed:19627125 ]
Qiao Y, Tu K, Feng W, Liu J, Xu Q, Tao L, Zhu H, Chen C, Wang J, Xue Y, Zhang Y: Polyketide and Prenylxanthone Derivatives from the Endophytic Fungus Aspergillus sp. TJ23. Chem Biodivers. 2018 Dec;15(12):e1800395. doi: 10.1002/cbdv.201800395. Epub 2018 Dec 7. [PubMed:30294975 ]
Pornpakakul S, Liangsakul J, Ngamrojanavanich N, Roengsumran S, Sihanonth P, Piapukiew J, Sangvichien E, Puthong S, Petsom A: Cytotoxic activity of four xanthones from Emericella variecolor, an endophytic fungus isolated from Croton oblongifolius. Arch Pharm Res. 2006 Feb;29(2):140-4. doi: 10.1007/BF02974275. [PubMed:16526278 ]
LOTUS database [Link]

Showing NP-Card for (3s,4r)-4,6-dihydroxy-9-[(2s)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one (NP0295646)

MOL for NP0295646 ((3s,4r)-4,6-dihydroxy-9-[(2s)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

3D MOL for NP0295646 ((3s,4r)-4,6-dihydroxy-9-[(2s)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

3D SDF for NP0295646 ((3s,4r)-4,6-dihydroxy-9-[(2s)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

3D-SDF for NP0295646 ((3s,4r)-4,6-dihydroxy-9-[(2s)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

PDB for NP0295646 ((3s,4r)-4,6-dihydroxy-9-[(2s)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

3D PDB for NP0295646 ((3s,4r)-4,6-dihydroxy-9-[(2s)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

SMILES for NP0295646 ((3s,4r)-4,6-dihydroxy-9-[(2s)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

INCHI for NP0295646 ((3s,4r)-4,6-dihydroxy-9-[(2s)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

Structure for NP0295646 ((3s,4r)-4,6-dihydroxy-9-[(2s)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)

3D Structure for NP0295646 ((3s,4r)-4,6-dihydroxy-9-[(2s)-2-hydroxy-3-methoxy-3-methylbutyl]-12-methyl-3-(prop-1-en-2-yl)-3,4-dihydro-2h-1,10-dioxatetraphen-5-one)