NP-MRD: Showing NP-Card for (1s,4s,4as,9ar)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one (NP0216375)

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Record Information

Version

2.0

Created at

2022-09-05 16:18:27 UTC

Updated at

2022-09-05 16:18:27 UTC

NP-MRD ID

NP0216375

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,4as,9ar)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one

Description

Mangrovamide J 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. (1s,4s,4as,9ar)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one was first documented in 2019 (PMID: 30419411). Based on a literature review very few articles have been published on Mangrovamide J.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    4.2736    0.0957   -0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129    0.4060    0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4236    1.5948   -0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9904    1.9686   -0.2585 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8064    2.5612    0.9903 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1758    0.7304   -0.4381 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5028    0.1654   -1.6681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2863    0.9908   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7929    2.1125   -0.3415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1814   -0.1801   -0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4871   -0.1120   -0.8753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0342    1.0688   -1.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2887   -1.2720   -0.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7410   -2.4640   -0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4305   -2.5041   -0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6013   -1.3774   -0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000   -1.4476    0.3488 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4921   -0.3198    0.6231 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0563    0.1988    2.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9501   -0.6273    0.6565 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1560   -1.8184   -0.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8357    0.7250    0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227    0.3651   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5032   -0.9486    0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1098    2.3126   -0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6935    2.6850   -1.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6334    2.6155    1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    0.7079   -2.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7166    1.9766   -1.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3182   -1.1601   -1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3756   -3.3395   -0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9801   -3.4340    0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7450    0.9490    1.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4166   -0.6366    2.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107    0.5476    2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2548   -0.7812    1.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3405   -2.3547   -0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 20  2  1  0
 18  6  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  6
  5 27  1  0
  7 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  1
 21 37  1  0
M  END


  Mrv1652309052218182D          

 21 23  0  0  1  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   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
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0216375

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@H](O)[C@]2(O)C(=O)C3=C(O)C=CC=C3O[C@@]2(C)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O6/c1-7-6-10(17)15(20)13(19)11-8(16)4-3-5-9(11)21-14(15,2)12(7)18/h3-6,10,12,16-18,20H,1-2H3/t10-,12-,14-,15-/m0/s1

> <INCHI_KEY>
VVXQWRWWHQGOBK-LVGORTOPSA-N

> <FORMULA>
C15H16O6

> <MOLECULAR_WEIGHT>
292.287

> <EXACT_MASS>
292.094688235

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.46430762626037

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,4aS,9aR)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-4,4a,9,9a-tetrahydro-1H-xanthen-9-one

> <JCHEM_LOGP>
0.6975238330000006

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.922333136384196

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.622982088242212

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5319375113805593

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
73.2131

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,4aS,9aR)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8   18                                             
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    6   19   20                                             
CONECT   19   18                                                            
CONECT   20   18    2   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₆

Average Mass

292.2870 Da

Monoisotopic Mass

292.09469 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=C[C@H](O)[C@]2(O)C(=O)C3=C(O)C=CC=C3O[C@@]2(C)[C@H]1O

InChI Identifier

InChI=1S/C15H16O6/c1-7-6-10(17)15(20)13(19)11-8(16)4-3-5-9(11)21-14(15,2)12(7)18/h3-6,10,12,16-18,20H,1-2H3/t10-,12-,14-,15-/m0/s1

InChI Key

VVXQWRWWHQGOBK-LVGORTOPSA-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 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
Chromone
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
Oxacycle
Polyol
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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

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

62934189

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139590242

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Padhi S, Masi M, Cimmino A, Tuzi A, Jena S, Tayung K, Evidente A: Funiculosone, a substituted dihydroxanthene-1,9-dione with two of its analogues produced by an endolichenic fungus Talaromyces funiculosus and their antimicrobial activity. Phytochemistry. 2019 Jan;157:175-183. doi: 10.1016/j.phytochem.2018.10.031. Epub 2018 Nov 9. [PubMed:30419411 ]
LOTUS database [Link]

Showing NP-Card for (1s,4s,4as,9ar)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one (NP0216375)

MOL for NP0216375 ((1s,4s,4as,9ar)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one)

3D MOL for NP0216375 ((1s,4s,4as,9ar)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one)

3D SDF for NP0216375 ((1s,4s,4as,9ar)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one)

3D-SDF for NP0216375 ((1s,4s,4as,9ar)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one)

PDB for NP0216375 ((1s,4s,4as,9ar)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one)

3D PDB for NP0216375 ((1s,4s,4as,9ar)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one)

SMILES for NP0216375 ((1s,4s,4as,9ar)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one)

INCHI for NP0216375 ((1s,4s,4as,9ar)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one)

Structure for NP0216375 ((1s,4s,4as,9ar)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one)

3D Structure for NP0216375 ((1s,4s,4as,9ar)-1,4,8,9a-tetrahydroxy-3,4a-dimethyl-1,4-dihydroxanthen-9-one)