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Showing NP-Card for Andibenin B (NP0050367)

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Record Information
Version2.0
Created at2022-04-27 20:55:56 UTC
Updated at2022-04-27 20:55:56 UTC
NP-MRD IDNP0050367
Secondary Accession NumbersNone
Natural Product Identification
Common NameAndibenin B
Description(1S,4R,5R,6R,8R,10S,16R)-5-hydroxy-2',2',5,8,10-pentamethyl-2',6'-dihydro-14-oxaspiro[pentacyclo[8.6.1.0¹,⁶.0⁸,¹⁶.0¹²,¹⁶]Heptadecane-4,3'-pyra]-11-ene-6',9,13-trione belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. Andibenin B is found in Aspergillus variecolor. Based on a literature review very few articles have been published on (1S,4R,5R,6R,8R,10S,16R)-5-hydroxy-2',2',5,8,10-pentamethyl-2',6'-dihydro-14-oxaspiro[pentacyclo[8.6.1.0¹,⁶.0⁸,¹⁶.0¹²,¹⁶]Heptadecane-4,3'-pyra]-11-ene-6',9,13-trione.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050367 (Andibenin B)


  Mrv1652304272222552D          

 31 36  0  0  1  0            999 V2000
    6.2706    0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4663    0.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2234    1.3094    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7847    1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5890    1.7303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8319    0.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6362    0.7580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9403    2.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000    2.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9983    2.0985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1866    2.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5244    1.6470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7584    0.8497    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6290    0.7076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4952   -0.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2166    0.1285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274    0.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2072    1.2181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6381    1.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8851    1.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0024    2.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7897    2.8667    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2580    2.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848    2.4688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4808    2.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920    3.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1645    1.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4031    1.7016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3540    0.5781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1890    0.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4396    0.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 13 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 22 25  1  0  0  0  0
 12 25  1  1  0  0  0
 22 26  1  1  0  0  0
 20 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 19 30  1  0  0  0  0
 18 31  1  6  0  0  0
M  END
Download

3D MOL for NP0050367 (Andibenin B)

Download
3D SDF for NP0050367 (Andibenin B)

  Mrv1652304272222552D          

 31 36  0  0  1  0            999 V2000
    6.2706    0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4663    0.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2234    1.3094    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7847    1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5890    1.7303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8319    0.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6362    0.7580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9403    2.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000    2.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9983    2.0985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1866    2.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5244    1.6470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7584    0.8497    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6290    0.7076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4952   -0.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2166    0.1285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274    0.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2072    1.2181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6381    1.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8851    1.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0024    2.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7897    2.8667    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2580    2.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848    2.4688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4808    2.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920    3.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1645    1.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4031    1.7016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3540    0.5781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1890    0.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4396    0.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 13 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 22 25  1  0  0  0  0
 12 25  1  1  0  0  0
 22 26  1  1  0  0  0
 20 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 19 30  1  0  0  0  0
 18 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050367

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12C[C@@H]3[C@]4(CC[C@@]5(C=CC(=O)OC5(C)C)[C@]3(C)O)C[C@@](C)(C=C3C(=O)OC[C@@]143)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O6/c1-19(2)24(7-6-16(26)31-19)9-8-23-12-20(3)10-14-17(27)30-13-25(14,23)21(4,18(20)28)11-15(23)22(24,5)29/h6-7,10,15,29H,8-9,11-13H2,1-5H3/t15-,20+,21-,22+,23-,24+,25+/m0/s1

> <INCHI_KEY>
FJRSJHTWTJSDAB-DWBMWQIASA-N

> <FORMULA>
C25H30O6

> <MOLECULAR_WEIGHT>
426.509

> <EXACT_MASS>
426.204238686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
44.247571516145285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4R,5R,6R,8R,10S,16R)-5-hydroxy-2',2',5,8,10-pentamethyl-2',6'-dihydro-14-oxaspiro[pentacyclo[8.6.1.0^{1,6}.0^{8,16}.0^{12,16}]heptadecane-4,3'-pyra]-11-ene-6',9,13-trione

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.931161688333333

> <ALOGPS_LOGS>
-4.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.197340674457415

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1498831889923258

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
112.58869999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,5R,6R,8R,10S,16R)-5-hydroxy-2',2',5,8,10-pentamethyl-14-oxaspiro[pentacyclo[8.6.1.0^{1,6}.0^{8,16}.0^{12,16}]heptadecane-4,3'-pyra]-11-ene-6',9,13-trione

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0050367 (Andibenin B)
Download
PDB for NP0050367 (Andibenin B)
HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      11.705   0.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.204   0.973   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.750   2.444   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.798   3.573   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      12.299   3.230   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.753   1.758   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.254   1.415   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.089   5.085   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.707   4.659   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.330   3.917   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.815   4.147   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.579   3.074   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.016   1.586   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.641   1.321   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.391  -0.199   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.738   0.240   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.464   0.977   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.120   2.274   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924   2.464   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.519   3.407   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.738   5.063   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.207   5.351   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.215   4.071   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.772   4.608   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.497   4.610   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.518   6.159   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.174   2.584   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.752   3.176   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.528   1.079   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.086   0.972   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.687   1.709   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10   14                                             
CONECT    4    3    5    8    9                                             
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19   25                                             
CONECT   13   12   14   17                                                  
CONECT   14   13    3   15   16                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19   23   31                                             
CONECT   19   18   12   20   30                                             
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25   26                                             
CONECT   23   22   18   24                                                  
CONECT   24   23                                                            
CONECT   25   22   12                                                       
CONECT   26   22                                                            
CONECT   27   20   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   19                                                       
CONECT   31   18                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

Download
3D PDB for NP0050367 (Andibenin B)
Download
SMILES for NP0050367 (Andibenin B)
C[C@@]12C[C@@H]3[C@]4(CC[C@@]5(C=CC(=O)OC5(C)C)[C@]3(C)O)C[C@@](C)(C=C3C(=O)OC[C@@]143)C2=O
Download
INCHI for NP0050367 (Andibenin B)
InChI=1S/C25H30O6/c1-19(2)24(7-6-16(26)31-19)9-8-23-12-20(3)10-14-17(27)30-13-25(14,23)21(4,18(20)28)11-15(23)22(24,5)29/h6-7,10,15,29H,8-9,11-13H2,1-5H3/t15-,20+,21-,22+,23-,24+,25+/m0/s1
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC25H30O6
Average Mass426.5090 Da
Monoisotopic Mass426.20424 Da
IUPAC Name(1S,4R,5R,6R,8R,10S,16R)-5-hydroxy-2',2',5,8,10-pentamethyl-2',6'-dihydro-14-oxaspiro[pentacyclo[8.6.1.0^{1,6}.0^{8,16}.0^{12,16}]heptadecane-4,3'-pyra]-11-ene-6',9,13-trione
Traditional Name(1S,4R,5R,6R,8R,10S,16R)-5-hydroxy-2',2',5,8,10-pentamethyl-14-oxaspiro[pentacyclo[8.6.1.0^{1,6}.0^{8,16}.0^{12,16}]heptadecane-4,3'-pyra]-11-ene-6',9,13-trione
CAS Registry NumberNot Available
SMILES
C[C@@]12C[C@@H]3[C@]4(CC[C@@]5(C=CC(=O)OC5(C)C)[C@]3(C)O)C[C@@](C)(C=C3C(=O)OC[C@@]143)C2=O
InChI Identifier
InChI=1S/C25H30O6/c1-19(2)24(7-6-16(26)31-19)9-8-23-12-20(3)10-14-17(27)30-13-25(14,23)21(4,18(20)28)11-15(23)22(24,5)29/h6-7,10,15,29H,8-9,11-13H2,1-5H3/t15-,20+,21-,22+,23-,24+,25+/m0/s1
InChI KeyFJRSJHTWTJSDAB-DWBMWQIASA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aspergillus stellatusFungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassPyranones and derivatives  
Direct ParentDihydropyranones  
Alternative Parents
Substituents
  • Cyclohexenone
    • 

  • Dihydropyranone
    • 

  • Gamma butyrolactone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Cyclic alcohol
    • 

  • Lactone
    • 

  • Ketone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.7ALOGPS
logP2.93ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)14.2ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area89.9 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity112.59 m³·mol⁻¹ChemAxon
Polarizability44.25 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162874039  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available