NP-MRD: Showing NP-Card for (1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione (NP0223852)

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Record Information

Version

2.0

Created at

2022-09-06 02:04:04 UTC

Updated at

2022-09-06 02:04:04 UTC

NP-MRD ID

NP0223852

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione

Description

Dehydroaustinol, also known as austinol, belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. (1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione is found in Aspergillus ustus. (1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione was first documented in 2007 (PMID: 17277172). Based on a literature review a significant number of articles have been published on Dehydroaustinol (PMID: 34343886) (PMID: 33563821) (PMID: 30044771) (PMID: 28674377) (PMID: 28467349) (PMID: 28233494).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204042D          

 33 38  0  0  1  0            999 V2000
    3.0298    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8157    1.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0186    1.4525    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5749    0.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7541    1.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2217    0.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202   -0.0399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1180    1.5496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373    2.2679    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4055    3.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9402    2.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125    3.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    2.0148    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0979    2.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044    3.0856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6948    1.6865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    0.9706    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5957    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8045    2.2492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4001    2.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3874    2.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845    2.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3986    1.8234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9815    2.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7786    2.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9927    1.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7898    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4098    0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6127    1.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3447    0.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6278    0.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1728    1.4548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8370    0.7013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 11  1  6  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  1  0  0  0
 13 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
  2 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  9 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END


  Mrv1652309062204042D          

 33 38  0  0  1  0            999 V2000
    3.0298    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8157    1.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0186    1.4525    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5749    0.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7541    1.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2217    0.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202   -0.0399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1180    1.5496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373    2.2679    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4055    3.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9402    2.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125    3.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    2.0148    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0979    2.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044    3.0856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6948    1.6865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    0.9706    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5957    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8045    2.2492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4001    2.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3874    2.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845    2.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3986    1.8234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9815    2.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7786    2.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9927    1.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7898    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4098    0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6127    1.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3447    0.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6278    0.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1728    1.4548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8370    0.7013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 11  1  6  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  1  0  0  0
 13 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
  2 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  9 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0223852

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1OC(=O)[C@]23C(=C)[C@]4(C)OC(=O)C12O[C@]1([C@@H]4O)C(=C)[C@@]2(CC[C@]31C)C=CC(=O)OC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O8/c1-12-21(7)16(27)24-13(2)22(9-8-15(26)31-19(22,4)5)11-10-20(24,6)23(12)17(28)30-14(3)25(23,33-24)18(29)32-21/h8-9,14,16,27H,1-2,10-11H2,3-7H3/t14-,16-,20-,21+,22+,23+,24+,25?/m1/s1

> <INCHI_KEY>
IQBUQLYYAHHCGX-GETWQMLSSA-N

> <FORMULA>
C25H28O8

> <MOLECULAR_WEIGHT>
456.491

> <EXACT_MASS>
456.178417862

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
44.96399421493757

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.0779141956666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.740392045754692

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7871525191868978

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000001

> <JCHEM_REFRACTIVITY>
112.66229999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       5.656   0.827   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.256   2.314   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.768   2.711   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.940   1.429   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.408   2.041   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.414   1.398   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.038  -0.074   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.220   2.893   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.816   4.233   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.757   5.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.755   5.142   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.450   6.516   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.568   3.761   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.183   4.269   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.568   5.760   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.297   3.148   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.453   1.812   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.112   0.420   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.368   4.198   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.613   5.541   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.456   5.288   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.944   4.891   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.344   3.404   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.432   4.493   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.920   4.096   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.320   2.609   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.808   2.211   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       8.232   1.519   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.744   1.916   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.244   0.460   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.772   0.377   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.189   2.716   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.562   1.309   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   19   32                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   13   17                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11   32                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    5   14   19                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    5   18                                                  
CONECT   18   17                                                            
CONECT   19   13    3   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    2   24   29                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23   30   31                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    9    3   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Value	Source
Austinol	MeSH

Chemical Formula

C₂₅H₂₈O₈

Average Mass

456.4910 Da

Monoisotopic Mass

456.17842 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@H]1OC(=O)[C@]23C(=C)[C@]4(C)OC(=O)C12O[C@]1([C@@H]4O)C(=C)[C@@]2(CC[C@]31C)C=CC(=O)OC2(C)C

InChI Identifier

InChI=1S/C25H28O8/c1-12-21(7)16(27)24-13(2)22(9-8-15(26)31-19(22,4)5)11-10-20(24,6)23(12)17(28)30-14(3)25(23,33-24)18(29)32-21/h8-9,14,16,27H,1-2,10-11H2,3-7H3/t14-,16-,20-,21+,22+,23+,24+,25?/m1/s1

InChI Key

IQBUQLYYAHHCGX-GETWQMLSSA-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 ustus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Furopyran
Furofuran
Oxepane
Delta_valerolactone
Dioxepane
Dihydropyranone
Delta valerolactone
1,4-dioxepane
Pyran
Oxane
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Furan
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.08	ChemAxon
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	112.66 m³·mol⁻¹	ChemAxon
Polarizability	44.96 Å³	ChemAxon
Number of Rings	6	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

23550436

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25235987

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mo S, Yin J, Ye Z, Li F, Lin S, Zhang S, Yang B, Yao J, Wang J, Hu Z, Zhang Y: Asperanstinoids A-E: Undescribed 3,5-dimethylorsellinic acid-based meroterpenoids from Aspergillus calidoustus. Phytochemistry. 2021 Jul 31;190:112892. doi: 10.1016/j.phytochem.2021.112892. [PubMed:34343886 ]
Marquez-Fernandez O, Trigos A, Ramos-Balderas JL, Viniegra-Gonzalez G, Deising HB, Aguirre J: Phosphopantetheinyl transferase CfwA/NpgA is required for Aspergillus nidulans secondary metabolism and asexual development. Eukaryot Cell. 2007 Apr;6(4):710-20. doi: 10.1128/EC.00362-06. Epub 2007 Feb 2. [PubMed:17277172 ]
Wu MY, Mead ME, Lee MK, Neuhaus GF, Adpressa DA, Martien JI, Son YE, Moon H, Amador-Noguez D, Han KH, Rokas A, Loesgen S, Yu JH, Park HS: Transcriptomic, Protein-DNA Interaction, and Metabolomic Studies of VosA, VelB, and WetA in Aspergillus nidulans Asexual Spores. mBio. 2021 Feb 9;12(1). pii: mBio.03128-20. doi: 10.1128/mBio.03128-20. [PubMed:33563821 ]
Thieme KG, Gerke J, Sasse C, Valerius O, Thieme S, Karimi R, Heinrich AK, Finkernagel F, Smith K, Bode HB, Freitag M, Ram AFJ, Braus GH: Velvet domain protein VosA represses the zinc cluster transcription factor SclB regulatory network for Aspergillus nidulans asexual development, oxidative stress response and secondary metabolism. PLoS Genet. 2018 Jul 25;14(7):e1007511. doi: 10.1371/journal.pgen.1007511. eCollection 2018 Jul. [PubMed:30044771 ]
Itoh E, Shigemoto R, Oinuma KI, Shimizu M, Masuo S, Takaya N: Sirtuin A regulates secondary metabolite production by Aspergillus nidulans. J Gen Appl Microbiol. 2017 Sep 5;63(4):228-235. doi: 10.2323/jgam.2016.11.002. Epub 2017 Jul 1. [PubMed:28674377 ]
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 ]
Valiante V, Mattern DJ, Schuffler A, Horn F, Walther G, Scherlach K, Petzke L, Dickhaut J, Guthke R, Hertweck C, Nett M, Thines E, Brakhage AA: Discovery of an Extended Austinoid Biosynthetic Pathway in Aspergillus calidoustus. ACS Chem Biol. 2017 May 19;12(5):1227-1234. doi: 10.1021/acschembio.7b00003. Epub 2017 Mar 15. [PubMed:28233494 ]
Chang PK, Scharfenstein LL, Mack B, Ehrlich KC: Deletion of the Aspergillus flavus orthologue of A. nidulans fluG reduces conidiation and promotes production of sclerotia but does not abolish aflatoxin biosynthesis. Appl Environ Microbiol. 2012 Nov;78(21):7557-63. doi: 10.1128/AEM.01241-12. Epub 2012 Aug 17. [PubMed:22904054 ]
Lo HC, Entwistle R, Guo CJ, Ahuja M, Szewczyk E, Hung JH, Chiang YM, Oakley BR, Wang CC: Two separate gene clusters encode the biosynthetic pathway for the meroterpenoids austinol and dehydroaustinol in Aspergillus nidulans. J Am Chem Soc. 2012 Mar 14;134(10):4709-20. doi: 10.1021/ja209809t. Epub 2012 Feb 29. [PubMed:22329759 ]
Rodriguez-Urra AB, Jimenez C, Nieto MI, Rodriguez J, Hayashi H, Ugalde U: Signaling the induction of sporulation involves the interaction of two secondary metabolites in Aspergillus nidulans. ACS Chem Biol. 2012 Mar 16;7(3):599-606. doi: 10.1021/cb200455u. Epub 2012 Jan 24. [PubMed:22234162 ]
Szewczyk E, Chiang YM, Oakley CE, Davidson AD, Wang CC, Oakley BR: Identification and characterization of the asperthecin gene cluster of Aspergillus nidulans. Appl Environ Microbiol. 2008 Dec;74(24):7607-12. doi: 10.1128/AEM.01743-08. Epub 2008 Oct 31. [PubMed:18978088 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione (NP0223852)

MOL for NP0223852 ((1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

3D MOL for NP0223852 ((1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

3D SDF for NP0223852 ((1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

3D-SDF for NP0223852 ((1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

PDB for NP0223852 ((1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

3D PDB for NP0223852 ((1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

SMILES for NP0223852 ((1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

INCHI for NP0223852 ((1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

Structure for NP0223852 ((1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)

3D Structure for NP0223852 ((1s,2r,5r,7r,8r,9s,13r)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1⁷,¹².0¹,¹².0²,⁷]heptadecane-5,3'-pyran]-6',11,15-trione)