NP-MRD: Showing NP-Card for paravallarine (NP0036006)

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Record Information

Version

2.0

Created at

2021-06-20 19:17:42 UTC

Updated at

2021-06-30 00:07:25 UTC

NP-MRD ID

NP0036006

Secondary Accession Numbers

None

Natural Product Identification

Common Name

paravallarine

Provided By

JEOL Database JEOL Logo

Description

(1R,2S,5S,6S,9R,12S,13R,16S)-6,13-dimethyl-16-(methylamino)-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]Icos-18-en-8-one belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. paravallarine is found in Holarrhena antidysenterica and Kibatalia laurifolia. paravallarine was first documented in 2011 (Phi, T. D., et al.). Based on a literature review very few articles have been published on (1R,2S,5S,6S,9R,12S,13R,16S)-6,13-dimethyl-16-(methylamino)-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]Icos-18-en-8-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121173D          

 58 62  0  0  0  0            999 V2000
    5.9736    4.2379   -1.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385    4.4775   -1.0002 N   0  0  1  0  0  0  0  0  0  0  0  0
    4.1662    3.2333   -0.5832 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1861    3.5777    0.5491 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4428    2.3344    1.0432 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6732    1.5584   -0.0641 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4650    2.4004   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6077    1.3461   -1.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313    0.1629   -1.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9702   -1.0749   -1.5374 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7941   -0.8279   -0.5802 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2068    0.1712    0.5378 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1243    0.2963    1.6430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3759   -1.0538    2.1831 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.1642   -2.3217    0.9180 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8797   -4.2083    0.1035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1724   -3.2494   -0.8655 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3291   -2.1449    0.0495 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4080    2.5469   -1.7347 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4787    5.1881   -2.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9156    2.5390   -0.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4652    4.3357    0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7309    4.0161    1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7547    2.6450    1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6793   -1.7896   -1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4  3  1  0  0  0  0
  4  5  1  0  0  0  0
  3 25  1  0  0  0  0
 24 23  1  0  0  0  0
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 22 21  1  0  0  0  0
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  6 12  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 12 11  1  0  0  0  0
 21 19  1  0  0  0  0
 19 18  1  0  0  0  0
 18 16  1  0  0  0  0
 25  8  1  0  0  0  0
 16 17  2  0  0  0  0
  6  5  1  0  0  0  0
  3  2  1  0  0  0  0
  6  8  1  0  0  0  0
  6  7  1  6  0  0  0
 11 41  1  6  0  0  0
 12 13  1  0  0  0  0
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 11 24  1  0  0  0  0
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M  END

     RDKit          3D

 58 62  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202121173D          

 58 62  0  0  0  0            999 V2000
    5.9736    4.2379   -1.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385    4.4775   -1.0002 N   0  0  1  0  0  0  0  0  0  0  0  0
    4.1662    3.2333   -0.5832 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1861    3.5777    0.5491 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.4650    2.4004   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3506   -0.5385   -0.2452 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4787    5.1881   -2.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6605    3.8333   -2.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7045    3.5628   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1723    4.9686   -0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9156    2.5390   -0.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4652    4.3357    0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7309    4.0161    1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7547    2.6450    1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1786    1.6690    1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637    2.7148    0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1650    1.8461   -1.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715    3.3198   -1.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    0.0651   -2.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6793   -1.7896   -1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904   -1.5297   -2.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0271   -0.3977   -1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -0.2753    1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7403    0.8511    1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4303   -1.5289    2.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1981   -0.8717    2.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6916   -2.8731    2.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4339   -4.3840    2.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627   -5.3632    2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6058   -4.9189    0.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5545   -3.8128    2.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705   -4.6274   -0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2180   -5.0500    0.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819   -2.8624   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371   -3.7497   -1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1912   -2.5597    0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7272    3.2609   -2.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1194    2.2379   -2.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  0  0  0  0
  3 25  1  0  0  0  0
 24 23  1  0  0  0  0
 23 22  1  0  0  0  0
 22 21  1  0  0  0  0
 15 21  1  0  0  0  0
  6 12  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  0  0  0  0
 21 19  1  0  0  0  0
 19 18  1  0  0  0  0
 18 16  1  0  0  0  0
 25  8  1  0  0  0  0
 16 17  2  0  0  0  0
  6  5  1  0  0  0  0
  3  2  1  0  0  0  0
  6  8  1  0  0  0  0
  6  7  1  6  0  0  0
 11 41  1  6  0  0  0
 12 13  1  0  0  0  0
 19 20  1  0  0  0  0
 11 24  1  0  0  0  0
 12 42  1  1  0  0  0
 15 14  1  0  0  0  0
 24 56  1  1  0  0  0
 14 13  1  0  0  0  0
 21 51  1  1  0  0  0
 15 16  1  6  0  0  0
 15 24  1  0  0  0  0
  2  1  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  3 30  1  1  0  0  0
 25 57  1  0  0  0  0
 25 58  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  9 38  1  0  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
 14 45  1  0  0  0  0
 14 46  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
 23 54  1  0  0  0  0
 23 55  1  0  0  0  0
 22 52  1  0  0  0  0
 22 53  1  0  0  0  0
 19 47  1  1  0  0  0
  2 29  1  0  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
  7 37  1  0  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
 20 50  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036006

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N(C([H])([H])[H])[C@]1([H])C([H])([H])C2=C([H])C([H])([H])[C@@]3([H])[C@]4([H])C([H])([H])C([H])([H])[C@]5([H])[C@@]([H])(OC(=O)[C@]45C([H])([H])C([H])([H])[C@]3([H])[C@@]2(C([H])([H])[H])C([H])([H])C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H33NO2/c1-13-17-6-7-19-16-5-4-14-12-15(23-3)8-10-21(14,2)18(16)9-11-22(17,19)20(24)25-13/h4,13,15-19,23H,5-12H2,1-3H3/t13-,15-,16+,17+,18-,19-,21-,22-/m0/s1

> <INCHI_KEY>
RSFPISDAJMWREU-CDFICMNGSA-N

> <FORMULA>
C22H33NO2

> <MOLECULAR_WEIGHT>
343.511

> <EXACT_MASS>
343.251129307

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.94719779861412

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,5S,6S,9R,12S,13R,16S)-6,13-dimethyl-16-(methylamino)-7-oxapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icos-18-en-8-one

> <ALOGPS_LOGP>
4.35

> <JCHEM_LOGP>
3.555719971666667

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.612677215119739

> <JCHEM_POLAR_SURFACE_AREA>
38.33

> <JCHEM_REFRACTIVITY>
99.44189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,6S,9R,12S,13R,16S)-6,13-dimethyl-16-(methylamino)-7-oxapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icos-18-en-8-one

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 58 62  0  0  0  0  0  0  0  0999 V2000
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   -0.8139   -1.9675    1.0433 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.1724   -3.2494   -0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3291   -2.1449    0.0495 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4080    2.5469   -1.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4787    5.1881   -2.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7309    4.0161    1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6793   -1.7896   -1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904   -1.5297   -2.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0271   -0.3977   -1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -0.2753    1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4303   -1.5289    2.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1981   -0.8717    2.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6916   -2.8731    2.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4339   -4.3840    2.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627   -5.3632    2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6058   -4.9189    0.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5545   -3.8128    2.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705   -4.6274   -0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2180   -5.0500    0.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819   -2.8624   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371   -3.7497   -1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1912   -2.5597    0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7272    3.2609   -2.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1194    2.2379   -2.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  4  5  1  0
  3 25  1  0
 24 23  1  0
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 22 21  1  0
 15 21  1  0
  6 12  1  0
  8  9  2  0
  9 10  1  0
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 18 16  1  0
 25  8  1  0
 16 17  2  0
  6  5  1  0
  3  2  1  0
  6  8  1  0
  6  7  1  6
 11 41  1  6
 12 13  1  0
 19 20  1  0
 11 24  1  0
 12 42  1  1
 15 14  1  0
 24 56  1  1
 14 13  1  0
 21 51  1  1
 15 16  1  6
 15 24  1  0
  2  1  1  0
  4 31  1  0
  4 32  1  0
  3 30  1  1
 25 57  1  0
 25 58  1  0
  5 33  1  0
  5 34  1  0
  9 38  1  0
 10 39  1  0
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 22 52  1  0
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  2 29  1  0
  7 35  1  0
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 20 48  1  0
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 20 50  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       5.974   4.238  -1.882  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.838   4.478  -1.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.166   3.233  -0.583  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.186   3.578   0.549  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.443   2.334   1.043  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.673   1.558  -0.064  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.465   2.400  -0.540  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.608   1.346  -1.262  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.731   0.163  -1.891  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.970  -1.075  -1.537  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.794  -0.828  -0.580  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.207   0.171   0.538  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.124   0.296   1.643  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.376  -1.054   2.183  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.814  -1.968   1.043  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.159  -1.500   0.480  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.351  -0.539  -0.245  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.164  -2.322   0.918  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.620  -3.290   1.815  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.438  -4.568   1.773  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.166  -3.410   1.405  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.880  -4.208   0.104  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.172  -3.249  -0.866  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.329  -2.145   0.050  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.408   2.547  -1.735  0.00  0.00           C+0
HETATM   26  H   UNK     0       6.479   5.188  -2.084  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.660   3.833  -2.849  0.00  0.00           H+0
HETATM   28  H   UNK     0       6.705   3.563  -1.426  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.172   4.969  -0.171  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.916   2.539  -0.178  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.465   4.336   0.218  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.731   4.016   1.395  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.755   2.645   1.839  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.179   1.669   1.515  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.164   2.715   0.300  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.165   1.846  -1.243  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.772   3.320  -1.049  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.418   0.065  -2.729  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.679  -1.790  -1.101  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.590  -1.530  -2.460  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.027  -0.398  -1.164  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.084  -0.275   1.034  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.740   0.851   1.266  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.518   0.873   2.487  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.430  -1.529   2.756  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.198  -0.872   2.886  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.692  -2.873   2.828  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.434  -4.384   2.190  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.963  -5.363   2.355  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.606  -4.919   0.750  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.555  -3.813   2.221  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.771  -4.627  -0.371  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.218  -5.050   0.341  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.882  -2.862  -1.606  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.637  -3.750  -1.406  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.191  -2.560   0.598  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.727   3.261  -2.215  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.119   2.238  -2.510  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1   29                                                  
CONECT    3    4   25    2   30                                             
CONECT    4    3    5   31   32                                             
CONECT    5    4    6   33   34                                             
CONECT    6   12    5    8    7                                             
CONECT    7    6   35   36   37                                             
CONECT    8    9   25    6                                                  
CONECT    9    8   10   38                                                  
CONECT   10    9   11   39   40                                             
CONECT   11   10   12   41   24                                             
CONECT   12    6   11   13   42                                             
CONECT   13   12   14   43   44                                             
CONECT   14   15   13   45   46                                             
CONECT   15   21   14   16   24                                             
CONECT   16   18   17   15                                                  
CONECT   17   16                                                            
CONECT   18   19   16                                                       
CONECT   19   21   18   20   47                                             
CONECT   20   19   48   49   50                                             
CONECT   21   22   15   19   51                                             
CONECT   22   23   21   52   53                                             
CONECT   23   24   22   54   55                                             
CONECT   24   23   11   56   15                                             
CONECT   25    3    8   57   58                                             
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    2                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37    7                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   19                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   22                                                            
CONECT   53   22                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   25                                                            
CONECT   58   25                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  124    0
END

RDKit          3D

58 62  0  0  0  0  0  0  0  0999 V2000
    5.9736    4.2379   -1.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385    4.4775   -1.0002 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1662    3.2333   -0.5832 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1861    3.5777    0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4428    2.3344    1.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6732    1.5584   -0.0641 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4650    2.4004   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6077    1.3461   -1.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313    0.1629   -1.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9702   -1.0749   -1.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7941   -0.8279   -0.5802 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2068    0.1712    0.5378 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1243    0.2963    1.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3759   -1.0538    2.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8139   -1.9675    1.0433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1589   -1.5001    0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3506   -0.5385   -0.2452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1642   -2.3217    0.9180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6202   -3.2898    1.8152 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4376   -4.5681    1.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1661   -3.4105    1.4047 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8797   -4.2083    0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724   -3.2494   -0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3291   -2.1449    0.0495 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4080    2.5469   -1.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4787    5.1881   -2.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6605    3.8333   -2.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7045    3.5628   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1723    4.9686   -0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9156    2.5390   -0.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4652    4.3357    0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7309    4.0161    1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7547    2.6450    1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1786    1.6690    1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637    2.7148    0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1650    1.8461   -1.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715    3.3198   -1.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    0.0651   -2.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6793   -1.7896   -1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904   -1.5297   -2.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0271   -0.3977   -1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -0.2753    1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7403    0.8511    1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5180    0.8728    2.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4303   -1.5289    2.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1981   -0.8717    2.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6916   -2.8731    2.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4339   -4.3840    2.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627   -5.3632    2.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6058   -4.9189    0.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5545   -3.8128    2.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705   -4.6274   -0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2180   -5.0500    0.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819   -2.8624   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371   -3.7497   -1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1912   -2.5597    0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7272    3.2609   -2.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1194    2.2379   -2.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  4  5  1  0
  3 25  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 15 21  1  0
  6 12  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 12 11  1  0
 21 19  1  0
 19 18  1  0
 18 16  1  0
 25  8  1  0
 16 17  2  0
  6  5  1  0
  3  2  1  0
  6  8  1  0
  6  7  1  6
 11 41  1  6
 12 13  1  0
 19 20  1  0
 11 24  1  0
 12 42  1  1
 15 14  1  0
 24 56  1  1
 14 13  1  0
 21 51  1  1
 15 16  1  6
 15 24  1  0
  2  1  1  0
  4 31  1  0
  4 32  1  0
  3 30  1  1
 25 57  1  0
 25 58  1  0
  5 33  1  0
  5 34  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 14 45  1  0
 14 46  1  0
 13 43  1  0
 13 44  1  0
 23 54  1  0
 23 55  1  0
 22 52  1  0
 22 53  1  0
 19 47  1  1
  2 29  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₂H₃₃NO₂

Average Mass

343.5110 Da

Monoisotopic Mass

343.25113 Da

IUPAC Name

(1R,2S,5S,6S,9R,12S,13R,16S)-6,13-dimethyl-16-(methylamino)-7-oxapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icos-18-en-8-one

Traditional Name

(1R,2S,5S,6S,9R,12S,13R,16S)-6,13-dimethyl-16-(methylamino)-7-oxapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icos-18-en-8-one

CAS Registry Number

Not Available

SMILES

[H]N(C([H])([H])[H])[C@]1([H])C([H])([H])C2=C([H])C([H])([H])[C@@]3([H])[C@]4([H])C([H])([H])C([H])([H])[C@]5([H])[C@@]([H])(OC(=O)[C@]45C([H])([H])C([H])([H])[C@]3([H])[C@@]2(C([H])([H])[H])C([H])([H])C1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H33NO2/c1-13-17-6-7-19-16-5-4-14-12-15(23-3)8-10-21(14,2)18(16)9-11-22(17,19)20(24)25-13/h4,13,15-19,23H,5-12H2,1-3H3/t13-,15-,16+,17+,18-,19-,21-,22-/m0/s1

InChI Key

RSFPISDAJMWREU-CDFICMNGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Holarrhena antidysenterica	KNApSAcK Database	22123792
Holarrhena pubescens	Plant	KNApSAcK
Kibatalia laurifolia	JEOL database	Phi, T. D., et al, J. Nat. Prod. 74, 1236 (2011)
Paravallaris microphylla	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Oxacycle
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Amine
Organic oxygen compound
Organooxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

steroid (CHEBI:67712 )
Steroidal alkaloids (C10814 )

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	4.35	ALOGPS
logP	3.56	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	10.61	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	99.44 m³·mol⁻¹	ChemAxon
Polarizability	40.95 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00002255

Chemspider ID

391283

KEGG Compound ID

C10814

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Phi, T. D., et al. (2011). Phi, T. D., et al, J. Nat. Prod. 74, 1236 (2011). J. Nat. Prod..

Showing NP-Card for paravallarine (NP0036006)

MOL for NP0036006 (paravallarine)

3D MOL for NP0036006 (paravallarine)

3D SDF for NP0036006 (paravallarine)

3D-SDF for NP0036006 (paravallarine)

PDB for NP0036006 (paravallarine)

3D PDB for NP0036006 (paravallarine)

SMILES for NP0036006 (paravallarine)

INCHI for NP0036006 (paravallarine)

Structure for NP0036006 (paravallarine)

3D Structure for NP0036006 (paravallarine)