NP-MRD: Showing NP-Card for variecolin (NP0312098)

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Record Information

Version

2.0

Created at

2022-09-11 08:35:21 UTC

Updated at

2022-09-11 08:35:21 UTC

NP-MRD ID

NP0312098

Secondary Accession Numbers

None

Natural Product Identification

Common Name

variecolin

Description

Variecolin belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. variecolin is found in Aspergillus stellatus, Aspergillus aurantiobrunneus and Aspergillus purpureus. variecolin was first documented in 2004 (PMID: 15497939). Based on a literature review a small amount of articles have been published on Variecolin (PMID: 27806646) (PMID: 29298482) (PMID: 29248948) (PMID: 24096306).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309112210352D          

 27 30  0  0  1  0            999 V2000
    1.7160   -3.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3541   -3.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1260   -3.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2202   -2.6314    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4829   -2.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6071   -1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4212   -1.3118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9678   -0.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8664   -0.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6905   -0.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0694   -1.3884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4202   -0.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8754   -1.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5699   -1.6573    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2819   -1.2406    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3633   -0.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8983   -1.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5672   -2.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9839   -3.2566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7462   -2.4632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3010   -3.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7723   -3.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215   -4.5816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4950   -3.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8005   -2.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6242   -2.0829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8001   -2.0446    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 18  1  1  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 11 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27  4  1  6  0  0  0
  7 27  1  0  0  0  0
M  END

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
   -3.8153    0.5272   -2.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6297   -0.2445   -1.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0251   -1.6723   -1.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0486    0.2998    0.1813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0439   -0.0877    1.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304   -0.1942    2.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8313    0.1408    2.1669 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6051    1.6005    2.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949   -0.7065    2.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5144   -0.4663    2.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454   -0.7039    0.7235 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1902   -2.1679    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466   -0.4978    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3882    0.9250    0.1369 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7745    1.1959    0.6195 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3960    0.1201    1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6379    1.4008   -0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6977    1.8334   -1.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0016    2.4259   -2.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548    1.4099   -1.2908 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8214    0.2775   -2.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7951   -0.2908   -3.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4269   -1.2390   -3.7687 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6461   -0.2873   -2.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292   -0.0766   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5087    0.1228    0.0470 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8111   -0.2868    0.6907 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2444    0.1043   -2.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5649    1.5828   -2.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9617   -2.0345   -2.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0986   -1.8158   -0.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3515   -2.3337   -0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0740    1.4176    0.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8504    0.6555    1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4380   -1.1240    1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6661    0.5401    3.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3021   -1.1838    3.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604    1.8668    2.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4133    2.0361    3.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6334    2.1939    1.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1101   -1.7441    2.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7214   -0.3039    3.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433    0.5707    2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2885   -1.1210    2.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1213   -2.7719    0.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405   -2.2897   -0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2968   -2.6441    1.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761   -1.1616   -0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5957   -0.9133    1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925    1.5643    0.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489    2.1472    1.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4221    0.5043    1.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -0.0524    2.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6122   -0.8171    0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0891    0.4435   -0.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4255    2.1513   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583    2.2632   -1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7783    0.1382   -3.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -1.0955   -2.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3199   -0.8499   -1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0039    0.9013   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2877    1.1971    0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8830   -1.3798    0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  1
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  1  6
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 21  2  0
 21 22  1  0
 22 23  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 14 15  1  0
 26 11  1  0
 21 20  1  0
 27  7  1  0
 16 52  1  0
 16 53  1  0
 16 54  1  0
 15 51  1  1
 17 55  1  0
 17 56  1  0
 20 57  1  1
 14 50  1  1
 13 48  1  0
 13 49  1  0
 12 45  1  0
 12 46  1  0
 12 47  1  0
 10 43  1  0
 10 44  1  0
  9 41  1  0
  9 42  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  6 36  1  0
  6 37  1  0
  5 34  1  0
  5 35  1  0
  4 33  1  6
 27 63  1  1
 26 62  1  6
 25 60  1  0
 25 61  1  0
 24 59  1  0
 22 58  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  1 28  1  0
  1 29  1  0
M  END

  Mrv1652309112210352D          

 27 30  0  0  1  0            999 V2000
    1.7160   -3.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3541   -3.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1260   -3.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2202   -2.6314    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4829   -2.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6071   -1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4212   -1.3118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9678   -0.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8664   -0.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6905   -0.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0694   -1.3884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4202   -0.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8754   -1.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5699   -1.6573    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2819   -1.2406    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3633   -0.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8983   -1.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5672   -2.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9839   -3.2566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7462   -2.4632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3010   -3.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7723   -3.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215   -4.5816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4950   -3.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8005   -2.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6242   -2.0829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8001   -2.0446    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 18  1  1  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 11 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27  4  1  6  0  0  0
  7 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0312098

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC(=O)[C@@H]2[C@H]1C[C@@]1(C)CC[C@]3(C)CC[C@@H]([C@H]3[C@@H]1C\C=C2\C=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O2/c1-15(2)18-8-9-24(4)10-11-25(5)13-19-16(3)12-21(27)22(19)17(14-26)6-7-20(25)23(18)24/h6,14,16,18-20,22-23H,1,7-13H2,2-5H3/b17-6-/t16-,18+,19-,20-,22-,23-,24-,25+/m0/s1

> <INCHI_KEY>
XAYQASOMEVLRKN-NOJNFTMQSA-N

> <FORMULA>
C25H36O2

> <MOLECULAR_WEIGHT>
368.561

> <EXACT_MASS>
368.271530399

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
43.60195008931774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,4S,7R,8E,11S,12S,13S,16S)-1,4,16-trimethyl-6-oxo-13-(prop-1-en-2-yl)tetracyclo[9.7.0.0^{3,7}.0^{12,16}]octadec-8-ene-8-carbaldehyde

> <JCHEM_LOGP>
5.215100651333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.614003084105875

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9637578276217535

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
110.92919999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4S,7R,8E,11S,12S,13S,16S)-1,4,16-trimethyl-6-oxo-13-(prop-1-en-2-yl)tetracyclo[9.7.0.0^{3,7}.0^{12,16}]octadec-8-ene-8-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       3.203  -7.408   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.394  -6.432   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.835  -6.975   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.144  -4.912   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.768  -4.221   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.000  -2.699   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.520  -2.449   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.673  -1.162   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.351  -1.152   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.889  -1.224   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.596  -2.592   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.251  -1.198   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.101  -2.263   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.397  -3.094   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.726  -2.316   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.878  -0.783   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.877  -3.339   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.259  -4.750   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.037  -6.079   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.726  -4.598   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.895  -5.895   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.775  -7.159   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.120  -8.552   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.391  -6.224   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.094  -5.393   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.765  -3.888   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.227  -3.817   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   27                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   26                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14   21                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   11   27                                                  
CONECT   27   26    4    7                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₆O₂

Average Mass

368.5610 Da

Monoisotopic Mass

368.27153 Da

IUPAC Name

(1R,3S,4S,7R,8E,11S,12S,13S,16S)-1,4,16-trimethyl-6-oxo-13-(prop-1-en-2-yl)tetracyclo[9.7.0.0^{3,7}.0^{12,16}]octadec-8-ene-8-carbaldehyde

Traditional Name

(1R,3S,4S,7R,8E,11S,12S,13S,16S)-1,4,16-trimethyl-6-oxo-13-(prop-1-en-2-yl)tetracyclo[9.7.0.0^{3,7}.0^{12,16}]octadec-8-ene-8-carbaldehyde

CAS Registry Number

Not Available

SMILES

C[C@H]1CC(=O)[C@@H]2[C@H]1C[C@@]1(C)CC[C@]3(C)CC[C@@H]([C@H]3[C@@H]1C\C=C2\C=O)C(C)=C

InChI Identifier

InChI=1S/C25H36O2/c1-15(2)18-8-9-24(4)10-11-25(5)13-19-16(3)12-21(27)22(19)17(14-26)6-7-20(25)23(18)24/h6,14,16,18-20,22-23H,1,7-13H2,2-5H3/b17-6-/t16-,18+,19-,20-,22-,23-,24-,25+/m0/s1

InChI Key

XAYQASOMEVLRKN-NOJNFTMQSA-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 stellatus	LOTUS Database	35616633
Emericella aurantiobrunnea	LOTUS Database	35616633
Emericella purpurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Variecolin sesterterpenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

sesterterpenoid (CHEBI:66349 )

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	5.22	ChemAxon
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	110.93 m³·mol⁻¹	ChemAxon
Polarizability	43.6 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00033466

Chemspider ID

4980914

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Variecolin

METLIN ID

Not Available

PubChem Compound

6480205

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yoganathan K, Rossant C, Glover RP, Cao S, Vittal JJ, Ng S, Huang Y, Buss AD, Butler MS: Inhibition of the human chemokine receptor CCR5 by variecolin and variecolol and isolation of four new variecolin analogues, emericolins A-D, from Emericella aurantiobrunnea. J Nat Prod. 2004 Oct;67(10):1681-4. doi: 10.1021/np049844c. [PubMed:15497939 ]
Jouda JB, Fopossi JD, Kengne FM, Djama Mbazoa C, Golz C, Strohmann C, Fogue SK, Wandji J: Secondary metabolites from Aspergillus japonicus CAM231, an endophytic fungus associated with Garcinia preussii. Nat Prod Res. 2017 Apr;31(8):861-869. doi: 10.1080/14786419.2016.1250089. Epub 2016 Nov 3. [PubMed:27806646 ]
Krout MR, Henry CE, Jensen T, Wu KL, Virgil SC, Stoltz BM: Wolff/Cope Approach to the AB Ring of the Sesterterpenoid Variecolin. J Org Chem. 2018 Jul 6;83(13):6995-7009. doi: 10.1021/acs.joc.7b02972. Epub 2018 Jan 23. [PubMed:29298482 ]
Yodsing N, Lekphrom R, Sangsopha W, Aimi T, Boonlue S: Secondary Metabolites and Their Biological Activity from Aspergillus aculeatus KKU-CT2. Curr Microbiol. 2018 May;75(5):513-518. doi: 10.1007/s00284-017-1411-y. Epub 2017 Dec 16. [PubMed:29248948 ]
Li K, Wang C, Yin G, Gao S: Construction of the basic skeleton of ophiobolin A and variecolin. Org Biomol Chem. 2013 Nov 21;11(43):7550-8. doi: 10.1039/c3ob41693c. [PubMed:24096306 ]
LOTUS database [Link]

Showing NP-Card for variecolin (NP0312098)

MOL for NP0312098 (variecolin)

3D MOL for NP0312098 (variecolin)

3D SDF for NP0312098 (variecolin)

3D-SDF for NP0312098 (variecolin)

PDB for NP0312098 (variecolin)

3D PDB for NP0312098 (variecolin)

SMILES for NP0312098 (variecolin)

INCHI for NP0312098 (variecolin)

Structure for NP0312098 (variecolin)

3D Structure for NP0312098 (variecolin)