NP-MRD: Showing NP-Card for dehydroaustin (NP0217775)

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Record Information

Version

2.0

Created at

2022-09-05 18:13:40 UTC

Updated at

2022-09-05 18:13:40 UTC

NP-MRD ID

NP0217775

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dehydroaustin

Description

Dehydroaustin belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. dehydroaustin is found in Aegiceras corniculatum and Penicillium simplicissimum. dehydroaustin was first documented in 2008 (PMID: 18293447). Based on a literature review a small amount of articles have been published on Dehydroaustin (PMID: 21601895) (PMID: 28467349) (PMID: 20971131).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052220132D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052220132D          

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M  END
> <DATABASE_ID>
NP0217775

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1OC(=O)[C@@]23C(=C)[C@@]4(C)OC(=O)[C@@]12O[C@@]1([C@H]4OC(C)=O)C(=C)[C@]2(CC[C@@]31C)C=CC(=O)OC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O9/c1-13-23(8)18(33-16(4)28)26-14(2)24(10-9-17(29)34-21(24,5)6)12-11-22(26,7)25(13)19(30)32-15(3)27(25,36-26)20(31)35-23/h9-10,15,18H,1-2,11-12H2,3-8H3/t15-,18-,22-,23+,24+,25+,26+,27-/m0/s1

> <INCHI_KEY>
UMCNDSVRNDMSEX-DVMWOTGCSA-N

> <FORMULA>
C27H30O9

> <MOLECULAR_WEIGHT>
498.528

> <EXACT_MASS>
498.188982546

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.20688245185446

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,7S,8S,9R,12S,13S)-2,2',2',9,13-pentamethyl-6,16-dimethylidene-6',11,15-trioxo-2',6'-dihydro-10,14,17-trioxaspiro[pentacyclo[7.6.1.1^{7,12}.0^{1,12}.0^{2,7}]heptadecane-5,3'-pyran]-8-yl acetate

> <JCHEM_LOGP>
2.519039606000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.359306910969529

> <JCHEM_POLAR_SURFACE_AREA>
114.43000000000002

> <JCHEM_REFRACTIVITY>
121.81379999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,7S,8S,9R,12S,13S)-2,2',2',9,13-pentamethyl-6,16-dimethylidene-6',11,15-trioxo-10,14,17-trioxaspiro[pentacyclo[7.6.1.1^{7,12}.0^{1,12}.0^{2,7}]heptadecane-5,3'-pyran]-8-yl acetate

> <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       2.408  -2.045   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.938  -1.875   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.510  -0.218   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.317  -1.290   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.996  -2.082   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.673  -0.815   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.008   0.767   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.028   1.955   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.668   0.796   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.228   1.415   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.300  -0.353   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.779  -0.785   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.144  -2.281   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.892   0.280   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.004   1.344   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.483   0.912   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.848  -0.584   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.326  -1.015   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.735  -1.648   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.257  -1.216   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.723  -2.661   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.250  -2.756   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.526   1.776   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.048   2.207   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.935   1.143   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.871   2.256   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.085  -2.185   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.258  -3.183   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.979  -4.698   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.152  -5.696   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.528  -5.214   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.305  -2.690   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.298  -4.230   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.687  -2.215   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.589  -0.417   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.135   0.091   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4    9   25                                             
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10   35                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   25   27                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20   23                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   14   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    3   11   26                                             
CONECT   26   25                                                            
CONECT   27   11   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27    2   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34    9   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₉

Average Mass

498.5280 Da

Monoisotopic Mass

498.18898 Da

IUPAC Name

(1R,2S,5S,7S,8S,9R,12S,13S)-2,2',2',9,13-pentamethyl-6,16-dimethylidene-6',11,15-trioxo-2',6'-dihydro-10,14,17-trioxaspiro[pentacyclo[7.6.1.1^{7,12}.0^{1,12}.0^{2,7}]heptadecane-5,3'-pyran]-8-yl acetate

Traditional Name

(1R,2S,5S,7S,8S,9R,12S,13S)-2,2',2',9,13-pentamethyl-6,16-dimethylidene-6',11,15-trioxo-10,14,17-trioxaspiro[pentacyclo[7.6.1.1^{7,12}.0^{1,12}.0^{2,7}]heptadecane-5,3'-pyran]-8-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1OC(=O)[C@@]23C(=C)[C@@]4(C)OC(=O)[C@@]12O[C@@]1([C@H]4OC(C)=O)C(=C)[C@]2(CC[C@@]31C)C=CC(=O)OC2(C)C

InChI Identifier

InChI=1S/C27H30O9/c1-13-23(8)18(33-16(4)28)26-14(2)24(10-9-17(29)34-21(24,5)6)12-11-22(26,7)25(13)19(30)32-15(3)27(25,36-26)20(31)35-23/h9-10,15,18H,1-2,11-12H2,3-8H3/t15-,18-,22-,23+,24+,25+,26+,27-/m0/s1

InChI Key

UMCNDSVRNDMSEX-DVMWOTGCSA-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
Aegiceras corniculatum	LOTUS Database	35616633
Penicillium simplicissimum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Furopyran
Furofuran
1,4-dioxepane
Delta valerolactone
Dihydropyranone
Dioxepane
Delta_valerolactone
Oxepane
Gamma butyrolactone
Pyran
Oxane
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Ether
Oxacycle
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.52	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	114.43 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	121.81 m³·mol⁻¹	ChemAxon
Polarizability	49.21 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

122201239

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang G, Sun S, Zhu T, Lin Z, Gu J, Li D, Gu Q: Antiviral isoindolone derivatives from an endophytic fungus Emericella sp. associated with Aegiceras corniculatum. Phytochemistry. 2011 Aug;72(11-12):1436-42. doi: 10.1016/j.phytochem.2011.04.014. Epub 2011 May 23. [PubMed:21601895 ]
Long Y, Cui H, Liu X, Xiao Z, Wen S, She Z, Huang X: Acetylcholinesterase Inhibitory Meroterpenoid from a Mangrove Endophytic Fungus Aspergillus sp. 16-5c. Molecules. 2017 May 3;22(5). pii: molecules22050727. doi: 10.3390/molecules22050727. [PubMed:28467349 ]
Kataoka S, Furutani S, Hirata K, Hayashi H, Matsuda K: Three austin family compounds from Penicillium brasilianum exhibit selective blocking action on cockroach nicotinic acetylcholine receptors. Neurotoxicology. 2011 Jan;32(1):123-9. doi: 10.1016/j.neuro.2010.10.003. Epub 2010 Oct 30. [PubMed:20971131 ]
Geris R, Rodrigues-Fo E, Garcia da Silva HH, Garcia da Silva I: Larvicidal effects of fungal Meroterpenoids in the control of Aedes aegypti L., the main vector of dengue and Yellow fever. Chem Biodivers. 2008 Feb;5(2):341-5. doi: 10.1002/cbdv.200890032. [PubMed:18293447 ]
LOTUS database [Link]

Showing NP-Card for dehydroaustin (NP0217775)

MOL for NP0217775 (dehydroaustin)

3D MOL for NP0217775 (dehydroaustin)

3D SDF for NP0217775 (dehydroaustin)

3D-SDF for NP0217775 (dehydroaustin)

PDB for NP0217775 (dehydroaustin)

3D PDB for NP0217775 (dehydroaustin)

SMILES for NP0217775 (dehydroaustin)

INCHI for NP0217775 (dehydroaustin)

Structure for NP0217775 (dehydroaustin)

3D Structure for NP0217775 (dehydroaustin)