NP-MRD: Showing NP-Card for (1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione (NP0148063)

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Record Information

Version

2.0

Created at

2022-09-02 03:46:19 UTC

Updated at

2022-09-02 03:46:19 UTC

NP-MRD ID

NP0148063

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione

Description

(-)-Brevianamide B belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. (1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione is found in Penicillium brevicompactum. (1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione was first documented in 2007 (PMID: 17854197). Based on a literature review a small amount of articles have been published on (-)-Brevianamide B (PMID: 29172511) (PMID: 26916112) (PMID: 25734916).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022205462D          

 27 32  0  0  1  0            999 V2000
    5.1890   -0.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5061    0.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2183    0.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6786    0.9383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9084    0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1582    0.9507    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3393    0.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7930    1.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973    2.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1373    1.8618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8996    2.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9024    3.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6626    1.8536    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5007    2.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0230    1.3790    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5067    2.0473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2918    1.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0055    2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7207    1.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7223    0.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0086    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2933    0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5092    0.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2558   -0.0727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8855    1.7759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9398    1.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695    0.4910    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  1  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  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  2  0  0  0  0
 13 25  1  0  0  0  0
 25 26  2  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 50 55  0  0  0  0  0  0  0  0999 V2000
   -1.4128   -0.2268    1.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6163   -0.7466    0.5605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4207   -2.2069    0.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5911    0.0374    0.2457 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8093   -0.1752    1.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9923   -0.0534    0.0881 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2828    0.1912    0.7312 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7172    1.5610    0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7676    2.0517   -0.7463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750    1.0267   -0.8932 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426    0.7800   -1.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    1.4206   -2.7365 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8544   -0.3952   -1.2078 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4533   -0.5947   -1.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4227   -0.4807   -0.7044 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5837   -1.2950   -0.8122 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6657   -0.5308   -0.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9423   -0.8564    0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8080    0.1021    0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4240    1.4293    0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1614    1.7766    0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3152    0.8010   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9581    0.9110   -0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111    1.9792   -1.0573 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7570   -1.5215   -1.2605 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9425   -1.3130   -0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132   -2.1380   -0.9269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8341   -0.4526    2.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6703    0.8406    1.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3382   -0.8434    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1218   -2.4195    1.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0331   -2.7201   -0.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4330   -2.6752    0.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3244    1.1216    0.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7966   -1.1758    1.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8839    0.6045    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0759   -0.5665    0.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1627    0.2236    1.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7385    1.5478   -0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7075    2.3001    1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2602    3.0142   -0.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529    2.2286   -1.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869    0.0647   -2.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5104   -1.6532   -2.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314   -2.2607   -1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2794   -1.8739    0.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8013   -0.1240    1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0510    2.2158    1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8281    2.8049    0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9137   -1.7353   -1.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  6
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 13 25  1  0
 25 26  2  0
 26 27  1  0
 15  2  1  0
 15 23  1  1
 13  4  1  0
 22 17  1  0
 10  6  1  0
 26  6  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  6
  5 35  1  0
  5 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
 14 43  1  0
 14 44  1  0
 16 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 21 49  1  0
 27 50  1  0
M  END


  Mrv1652309022205462D          

 27 32  0  0  1  0            999 V2000
    5.1890   -0.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5061    0.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2183    0.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6786    0.9383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9084    0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1582    0.9507    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3393    0.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7930    1.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973    2.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1373    1.8618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8996    2.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9024    3.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6626    1.8536    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5007    2.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0230    1.3790    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5067    2.0473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2918    1.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0055    2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7207    1.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7223    0.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0086    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2933    0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5092    0.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2558   -0.0727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8855    1.7759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9398    1.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695    0.4910    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  1  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  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  2  0  0  0  0
 13 25  1  0  0  0  0
 25 26  2  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0148063

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@H]2C[C@]34CCCN3C(=O)[C@@]2(C[C@@]11NC2=CC=CC=C2C1=O)N=C4O

> <INCHI_IDENTIFIER>
InChI=1S/C21H23N3O3/c1-18(2)14-10-19-8-5-9-24(19)17(27)20(14,23-16(19)26)11-21(18)15(25)12-6-3-4-7-13(12)22-21/h3-4,6-7,14,22H,5,8-11H2,1-2H3,(H,23,26)/t14-,19+,20+,21+/m1/s1

> <INCHI_KEY>
MWOFPQAPILIIPR-LYARXQMPSA-N

> <FORMULA>
C21H23N3O3

> <MOLECULAR_WEIGHT>
365.433

> <EXACT_MASS>
365.173941613

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.78946818188905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2R,3'R,7'S)-13'-hydroxy-4',4'-dimethyl-1,3-dihydro-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-ene-3,8'-dione

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.385900203666666

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.129123487099472

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.230077605252277

> <JCHEM_PKA_STRONGEST_BASIC>
0.4679370474003687

> <JCHEM_POLAR_SURFACE_AREA>
82.0

> <JCHEM_REFRACTIVITY>
99.83899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,3'R,7'S)-13'-hydroxy-4',4'-dimethyl-1H-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-ene-3,8'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       9.686  -0.081   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.278   1.341   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.607   0.563   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.733   1.752   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.296   0.777   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.895   1.775   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.367   1.342   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.347   2.530   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.288   3.783   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.856   3.475   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       7.279   4.449   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.284   5.989   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.704   3.460   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.268   3.804   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.243   2.574   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      12.146   3.822   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      13.611   3.349   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.944   4.121   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.279   3.354   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.282   1.814   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.949   1.041   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.614   1.809   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.151   1.330   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.677  -0.136   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       7.253   3.315   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       7.354   1.912   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.530   0.916   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   15                                             
CONECT    3    2                                                            
CONECT    4    2    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10   26                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    4   14   25                                             
CONECT   14   13   15                                                       
CONECT   15   14    2   16   23                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22   15   24                                                  
CONECT   24   23                                                            
CONECT   25   13   26                                                       
CONECT   26   25    6   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Value	Source
Brevianamide b	MeSH

Chemical Formula

C₂₁H₂₃N₃O₃

Average Mass

365.4330 Da

Monoisotopic Mass

365.17394 Da

IUPAC Name

(1'S,2R,3'R,7'S)-13'-hydroxy-4',4'-dimethyl-1,3-dihydro-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-ene-3,8'-dione

Traditional Name

(1'S,2R,3'R,7'S)-13'-hydroxy-4',4'-dimethyl-1H-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-ene-3,8'-dione

CAS Registry Number

Not Available

SMILES

CC1(C)[C@H]2C[C@]34CCCN3C(=O)[C@@]2(C[C@@]11NC2=CC=CC=C2C1=O)N=C4O

InChI Identifier

InChI=1S/C21H23N3O3/c1-18(2)14-10-19-8-5-9-24(19)17(27)20(14,23-16(19)26)11-21(18)15(25)12-6-3-4-7-13(12)22-21/h3-4,6-7,14,22H,5,8-11H2,1-2H3,(H,23,26)/t14-,19+,20+,21+/m1/s1

InChI Key

MWOFPQAPILIIPR-LYARXQMPSA-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
Penicillium brevicompactum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Azaspirodecane
Indole or derivatives
Dihydroindole
Indolizidine
Dioxopiperazine
2,5-dioxopiperazine
Aryl alkyl ketone
Aryl ketone
Delta-lactam
N-alkylpiperazine
Piperidinone
Secondary aliphatic/aromatic amine
1,4-diazinane
Benzenoid
Piperazine
Piperidine
Pyrrolidine
Tertiary carboxylic acid amide
Vinylogous amide
Amino acid or derivatives
Secondary carboxylic acid amide
Lactam
Ketone
Carboxamide group
Secondary amine
Azacycle
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Amine
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.17	ALOGPS
logP	2.39	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.23	ChemAxon
pKa (Strongest Basic)	0.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	99.84 m³·mol⁻¹	ChemAxon
Polarizability	38.79 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21447236

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25163936

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Perkins JC, Wang X, Pike RD, Scheerer JR: Further Investigation of the Intermolecular Diels-Alder Cycloaddition for the Synthesis of Bicyclo[2.2.2]diazaoctane Alkaloids. J Org Chem. 2017 Dec 15;82(24):13656-13662. doi: 10.1021/acs.joc.7b02403. Epub 2017 Nov 27. [PubMed:29172511 ]
Robins JG, Kim KJ, Chinn AJ, Woo JS, Scheerer JR: Intermolecular Diels-Alder Cycloaddition for the Construction of Bicyclo[2.2.2]diazaoctane Structures: Formal Synthesis of Brevianamide B and Premalbrancheamide. J Org Chem. 2016 Mar 18;81(6):2293-301. doi: 10.1021/acs.joc.5b02744. Epub 2016 Feb 26. [PubMed:26916112 ]
Bultinck P, Cherblanc FL, Fuchter MJ, Herrebout WA, Lo YP, Rzepa HS, Siligardi G, Weimar M: Chiroptical studies on brevianamide B: vibrational and electronic circular dichroism confronted. J Org Chem. 2015 Apr 3;80(7):3359-67. doi: 10.1021/jo5022647. Epub 2015 Mar 17. [PubMed:25734916 ]
Greshock TJ, Williams RM: Improved biomimetic total synthesis of D,L-stephacidin A. Org Lett. 2007 Oct 11;9(21):4255-8. doi: 10.1021/ol701845t. Epub 2007 Sep 14. [PubMed:17854197 ]
LOTUS database [Link]

Showing NP-Card for (1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione (NP0148063)

MOL for NP0148063 ((1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

3D MOL for NP0148063 ((1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

3D SDF for NP0148063 ((1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

3D-SDF for NP0148063 ((1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

PDB for NP0148063 ((1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

3D PDB for NP0148063 ((1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

SMILES for NP0148063 ((1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

INCHI for NP0148063 ((1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

Structure for NP0148063 ((1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

3D Structure for NP0148063 ((1's,2r,3'r,7's)-13'-hydroxy-4',4'-dimethyl-1h-9',14'-diazaspiro[indole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)