NP-MRD: Showing NP-Card for Austalide A (NP0084944)

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Record Information

Version

2.0

Created at

2022-04-29 05:33:16 UTC

Updated at

2022-04-29 05:33:16 UTC

NP-MRD ID

NP0084944

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Austalide A

Description

Austalide A belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring. Austalide A is found in Aspergillus ustus. Based on a literature review very few articles have been published on Austalide A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207332D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292207332D          

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 12 19  1  6  0  0  0
  8 20  2  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 16  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 15 32  1  0  0  0  0
 30 33  1  0  0  0  0
 22 34  1  1  0  0  0
  3 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
  4 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084944

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC3=C(O[C@@]1(C)C[C@@H](OC(C)=O)[C@]14O[C@@](CC[C@]21C)(OC)OC4(C)C)C(C)=C1COC(=O)C1=C3OC

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O9/c1-14-17-13-33-23(30)20(17)22(31-7)16-11-18-25(5)9-10-27(32-8)36-24(3,4)28(25,37-27)19(34-15(2)29)12-26(18,6)35-21(14)16/h18-19H,9-13H2,1-8H3/t18-,19-,25-,26+,27+,28-/m1/s1

> <INCHI_KEY>
JVCNHGXAVMINTN-QBNAFFQBSA-N

> <FORMULA>
C28H36O9

> <MOLECULAR_WEIGHT>
516.587

> <EXACT_MASS>
516.235932739

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.01154281620171

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,16R,17R,20S)-13,20-dimethoxy-4,7,17,22,22-pentamethyl-11-oxo-5,10,21,23-tetraoxahexacyclo[18.2.1.0^{1,17}.0^{4,16}.0^{6,14}.0^{8,12}]tricosa-6(14),7,12-trien-2-yl acetate

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
4.011131000333336

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.662270731281257

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9410602358583193

> <JCHEM_POLAR_SURFACE_AREA>
98.75000000000003

> <JCHEM_REFRACTIVITY>
131.55319999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,16R,17R,20S)-13,20-dimethoxy-4,7,17,22,22-pentamethyl-11-oxo-5,10,21,23-tetraoxahexacyclo[18.2.1.0^{1,17}.0^{4,16}.0^{6,14}.0^{8,12}]tricosa-6(14),7,12-trien-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      11.672   4.946   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.407   3.429   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.589   2.442   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.325   0.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.879   0.395   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.614  -1.122   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.168  -1.652   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.697   1.382   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.251   0.853   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.069   1.840   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       5.888   2.829   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       5.606   1.307   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.505  -0.312   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.029  -0.921   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.736   0.054   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.583   1.147   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.656  -1.044   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.166  -0.658   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.840   0.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.961   2.900   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.780   3.887   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.334   3.357   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.157   4.368   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.691   3.840   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.554   4.878   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.883   6.382   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.746   7.420   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.351   6.849   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.292   2.299   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.657   2.678   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.186   4.125   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.742   1.328   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.286   3.380   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.608   4.873   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.114   2.659   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      14.792   1.276   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      13.686   0.204   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      13.903  -1.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4   35                                                  
CONECT    4    3    5   37                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   22                                             
CONECT   11   10                                                            
CONECT   12   10   13   19   29                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   32                                             
CONECT   16   15   29                                                       
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   12                                                            
CONECT   20    8    2   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   10   23   34                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   12   16   30                                             
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30   15                                                       
CONECT   33   30                                                            
CONECT   34   22                                                            
CONECT   35    3   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    4   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆O₉

Average Mass

516.5870 Da

Monoisotopic Mass

516.23593 Da

IUPAC Name

(1R,2R,4S,16R,17R,20S)-13,20-dimethoxy-4,7,17,22,22-pentamethyl-11-oxo-5,10,21,23-tetraoxahexacyclo[18.2.1.0^{1,17}.0^{4,16}.0^{6,14}.0^{8,12}]tricosa-6(14),7,12-trien-2-yl acetate

Traditional Name

(1R,2R,4S,16R,17R,20S)-13,20-dimethoxy-4,7,17,22,22-pentamethyl-11-oxo-5,10,21,23-tetraoxahexacyclo[18.2.1.0^{1,17}.0^{4,16}.0^{6,14}.0^{8,12}]tricosa-6(14),7,12-trien-2-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@]12CC3=C(O[C@@]1(C)C[C@@H](OC(C)=O)[C@]14O[C@@](CC[C@]21C)(OC)OC4(C)C)C(C)=C1COC(=O)C1=C3OC

InChI Identifier

InChI=1S/C28H36O9/c1-14-17-13-33-23(30)20(17)22(31-7)16-11-18-25(5)9-10-27(32-8)36-24(3,4)28(25,37-27)19(34-15(2)29)12-26(18,6)35-21(14)16/h18-19H,9-13H2,1-8H3/t18-,19-,25-,26+,27+,28-/m1/s1

InChI Key

JVCNHGXAVMINTN-QBNAFFQBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 ustus	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthenes

Alternative Parents

Substituents

Xanthene
Isobenzofuranone
Phthalide
Isocoumaran
Anisole
Alkyl aryl ether
Carboxylic acid orthoester
Ortho ester
Oxepane
Dicarboxylic acid or derivatives
Oxane
Benzenoid
Meta-dioxolane
Lactone
Carboxylic acid ester
Orthocarboxylic acid derivative
Oxacycle
Ether
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
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	3.74	ALOGPS
logP	4.01	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	13.66	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	98.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	131.55 m³·mol⁻¹	ChemAxon
Polarizability	54.01 Å³	ChemAxon
Number of Rings	6	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

C00054592

Chemspider ID

138996

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

157977

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Austalide A (NP0084944)

MOL for NP0084944 (Austalide A)

3D MOL for NP0084944 (Austalide A)

3D SDF for NP0084944 (Austalide A)

3D-SDF for NP0084944 (Austalide A)

PDB for NP0084944 (Austalide A)

3D PDB for NP0084944 (Austalide A)

SMILES for NP0084944 (Austalide A)

INCHI for NP0084944 (Austalide A)

Structure for NP0084944 (Austalide A)

3D Structure for NP0084944 (Austalide A)