NP-MRD: Showing NP-Card for (3s,4ar,8s,9as,9bs)-8-hydroxy-2-methyl-3-[(1e)-non-1-en-1-yl]-3h,4ah,7h,8h,9h,9ah,9bh-cyclopenta[f]chromen-5-one (NP0202991)

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Record Information

Version

2.0

Created at

2022-09-04 22:20:51 UTC

Updated at

2022-09-04 22:20:52 UTC

NP-MRD ID

NP0202991

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4ar,8s,9as,9bs)-8-hydroxy-2-methyl-3-[(1e)-non-1-en-1-yl]-3h,4ah,7h,8h,9h,9ah,9bh-cyclopenta[f]chromen-5-one

Description

Penostatin B belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (3s,4ar,8s,9as,9bs)-8-hydroxy-2-methyl-3-[(1e)-non-1-en-1-yl]-3h,4ah,7h,8h,9h,9ah,9bh-cyclopenta[f]chromen-5-one was first documented in 2012 (PMID: 22145647). Based on a literature review a small amount of articles have been published on Penostatin B (PMID: 24481115) (PMID: 25585160).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052200202D          

 25 27  0  0  1  0            999 V2000
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0446   -7.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7091   -8.7307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1216   -9.4452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8886   -8.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  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  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 21 20  1  1  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  2  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
    6.0300    2.3604    0.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1855    0.8774    0.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5117    0.1413   -0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0271    0.4300   -0.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140   -0.2798   -1.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4375   -1.7759   -1.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8633   -2.3200   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4425   -1.9533   -0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9187   -1.2119    0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5267   -0.8681    0.9363 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1084   -1.4381   -0.1701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031   -0.7329   -0.7819 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0015   -1.5758   -1.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104   -2.1935   -2.5802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4218   -1.6952   -1.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0060   -0.6921   -0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3352   -0.4101    0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3813    1.0900    0.1326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3101    1.5199    1.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9547    1.4162    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1419    0.4856   -0.2954 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8978   -0.0302    0.3302 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9526    1.0574    0.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7507    0.5893    1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262    1.4879    1.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0263    2.8850    0.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4841    2.7895    1.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5217    2.7059   -0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7206    0.5172    1.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2646    0.6351    0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0124    0.4215   -1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6886   -0.9461   -0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5897    0.1886    0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875    1.5199   -0.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938    0.0513   -2.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2227   -0.0463   -1.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4840   -2.1258   -1.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8821   -2.2072   -2.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4509   -2.0444    0.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151   -3.4412   -0.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -2.3111   -0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5754   -0.8580    1.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9306   -1.3156    1.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6362    0.0819   -1.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9930   -2.5917   -1.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4580   -0.8249    1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1576   -0.8043   -0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5645    1.5225   -0.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9802    0.7736    1.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7532    2.4481    0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7972    1.2133    1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265    0.9385   -1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1512   -0.7183    1.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2302    2.0926    0.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0704    2.4057    2.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0233    1.7759    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9674    0.9905    2.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  1  0
 18 17  1  0
 17 16  1  0
 16 15  2  0
 15 13  1  0
 13 14  2  0
 24 10  1  0
 16 21  1  0
 13 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  1
 12 44  1  6
 22 53  1  1
 23 54  1  0
 25 55  1  0
 25 56  1  0
 25 57  1  0
 21 52  1  6
 20 50  1  0
 20 51  1  0
 18 48  1  6
 19 49  1  0
 17 46  1  0
 17 47  1  0
 15 45  1  0
M  END


  Mrv1652309052200202D          

 25 27  0  0  1  0            999 V2000
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0446   -7.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7091   -8.7307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1216   -9.4452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8886   -8.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  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  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 21 20  1  1  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  2  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0202991

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC\C=C\[C@@H]1O[C@@H]2[C@@H](C=C1C)[C@@H]1C[C@H](O)CC1=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O3/c1-3-4-5-6-7-8-9-10-21-15(2)11-19-18-14-17(23)12-16(18)13-20(24)22(19)25-21/h9-11,13,17-19,21-23H,3-8,12,14H2,1-2H3/b10-9+/t17-,18-,19+,21+,22-/m1/s1

> <INCHI_KEY>
ONCGMAFAIBLDNP-NCHXIBIBSA-N

> <FORMULA>
C22H32O3

> <MOLECULAR_WEIGHT>
344.495

> <EXACT_MASS>
344.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.15938113569238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4aR,8S,9aS,9bS)-8-hydroxy-2-methyl-3-[(1E)-non-1-en-1-yl]-3H,4aH,5H,7H,8H,9H,9aH,9bH-cyclopenta[f]chromen-5-one

> <JCHEM_LOGP>
4.601002502

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.2653132715533

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.180122082807035

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3700017792388275

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
103.58099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4aR,8S,9aS,9bS)-8-hydroxy-2-methyl-3-[(1E)-non-1-en-1-yl]-3H,4aH,7H,8H,9H,9aH,9bH-cyclopenta[f]chromen-5-one

> <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       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      17.338 -11.550   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      18.672 -12.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      20.005 -10.010   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      21.339 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.483 -14.890   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.857 -16.297   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      22.627 -17.631   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      20.325 -16.136   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   12   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   10   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂O₃

Average Mass

344.4950 Da

Monoisotopic Mass

344.23514 Da

IUPAC Name

(3S,4aR,8S,9aS,9bS)-8-hydroxy-2-methyl-3-[(1E)-non-1-en-1-yl]-3H,4aH,5H,7H,8H,9H,9aH,9bH-cyclopenta[f]chromen-5-one

Traditional Name

(3S,4aR,8S,9aS,9bS)-8-hydroxy-2-methyl-3-[(1E)-non-1-en-1-yl]-3H,4aH,7H,8H,9H,9aH,9bH-cyclopenta[f]chromen-5-one

CAS Registry Number

Not Available

SMILES

CCCCCCC\C=C\[C@@H]1O[C@@H]2[C@@H](C=C1C)[C@@H]1C[C@H](O)CC1=CC2=O

InChI Identifier

InChI=1S/C22H32O3/c1-3-4-5-6-7-8-9-10-21-15(2)11-19-18-14-17(23)12-16(18)13-20(24)22(19)25-21/h9-11,13,17-19,21-23H,3-8,12,14H2,1-2H3/b10-9+/t17-,18-,19+,21+,22-/m1/s1

InChI Key

ONCGMAFAIBLDNP-NCHXIBIBSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Pyran
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxide
Hydrocarbon derivative
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	4.6	ChemAxon
pKa (Strongest Acidic)	16.18	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	103.58 m³·mol⁻¹	ChemAxon
Polarizability	41.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

8625628

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10450211

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen YP, Yang CG, Wei PY, Li L, Luo DQ, Zheng ZH, Lu XH: Penostatin derivatives, a novel kind of protein phosphatase 1b inhibitors isolated from solid cultures of the entomogenous fungus Isaria tenuipes. Molecules. 2014 Jan 29;19(2):1663-71. doi: 10.3390/molecules19021663. [PubMed:24481115 ]
Reddy DS, Padhi B, Mohapatra DK: Highly stereocontrolled synthesis of trans-2,6-disubstituted-5-methyl-3,6-dihydropyrans: stereoselective synthesis of the bicyclic core of penostatin B. J Org Chem. 2015 Feb 6;80(3):1365-74. doi: 10.1021/jo502101u. Epub 2015 Jan 28. [PubMed:25585160 ]
Fujioka K, Yokoe H, Yoshida M, Shishido K: Total synthesis of penostatin B. Org Lett. 2012 Jan 6;14(1):244-7. doi: 10.1021/ol203021c. Epub 2011 Dec 6. [PubMed:22145647 ]
LOTUS database [Link]

Showing NP-Card for (3s,4ar,8s,9as,9bs)-8-hydroxy-2-methyl-3-[(1e)-non-1-en-1-yl]-3h,4ah,7h,8h,9h,9ah,9bh-cyclopenta[f]chromen-5-one (NP0202991)

MOL for NP0202991 ((3s,4ar,8s,9as,9bs)-8-hydroxy-2-methyl-3-[(1e)-non-1-en-1-yl]-3h,4ah,7h,8h,9h,9ah,9bh-cyclopenta[f]chromen-5-one)

3D MOL for NP0202991 ((3s,4ar,8s,9as,9bs)-8-hydroxy-2-methyl-3-[(1e)-non-1-en-1-yl]-3h,4ah,7h,8h,9h,9ah,9bh-cyclopenta[f]chromen-5-one)

3D SDF for NP0202991 ((3s,4ar,8s,9as,9bs)-8-hydroxy-2-methyl-3-[(1e)-non-1-en-1-yl]-3h,4ah,7h,8h,9h,9ah,9bh-cyclopenta[f]chromen-5-one)

3D-SDF for NP0202991 ((3s,4ar,8s,9as,9bs)-8-hydroxy-2-methyl-3-[(1e)-non-1-en-1-yl]-3h,4ah,7h,8h,9h,9ah,9bh-cyclopenta[f]chromen-5-one)

PDB for NP0202991 ((3s,4ar,8s,9as,9bs)-8-hydroxy-2-methyl-3-[(1e)-non-1-en-1-yl]-3h,4ah,7h,8h,9h,9ah,9bh-cyclopenta[f]chromen-5-one)

3D PDB for NP0202991 ((3s,4ar,8s,9as,9bs)-8-hydroxy-2-methyl-3-[(1e)-non-1-en-1-yl]-3h,4ah,7h,8h,9h,9ah,9bh-cyclopenta[f]chromen-5-one)

SMILES for NP0202991 ((3s,4ar,8s,9as,9bs)-8-hydroxy-2-methyl-3-[(1e)-non-1-en-1-yl]-3h,4ah,7h,8h,9h,9ah,9bh-cyclopenta[f]chromen-5-one)

INCHI for NP0202991 ((3s,4ar,8s,9as,9bs)-8-hydroxy-2-methyl-3-[(1e)-non-1-en-1-yl]-3h,4ah,7h,8h,9h,9ah,9bh-cyclopenta[f]chromen-5-one)

Structure for NP0202991 ((3s,4ar,8s,9as,9bs)-8-hydroxy-2-methyl-3-[(1e)-non-1-en-1-yl]-3h,4ah,7h,8h,9h,9ah,9bh-cyclopenta[f]chromen-5-one)

3D Structure for NP0202991 ((3s,4ar,8s,9as,9bs)-8-hydroxy-2-methyl-3-[(1e)-non-1-en-1-yl]-3h,4ah,7h,8h,9h,9ah,9bh-cyclopenta[f]chromen-5-one)