NP-MRD: Showing NP-Card for (2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one (NP0154273)

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Record Information

Version

2.0

Created at

2022-09-02 11:03:38 UTC

Updated at

2022-09-02 11:03:38 UTC

NP-MRD ID

NP0154273

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one

Description

Iso-alpha-cyclopiazonic acid, also known as iso-a-cyclopiazonate, belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. (2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one was first documented in 2014 (PMID: 24983640). Based on a literature review very few articles have been published on Iso-alpha-cyclopiazonic acid (PMID: 26460559).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022213032D          

 25 29  0  0  1  0            999 V2000
    7.3596    0.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6596    0.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6877   -0.4050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9315    0.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1897    0.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0458   -0.3659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6171    1.0403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8048    1.1843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1542    0.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0960   -0.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2953   -0.3450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8587    0.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0464    0.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7649    1.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957    1.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2754    1.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3896    0.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9259    2.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6906    2.0013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4324    2.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9958    3.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0829    2.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0050    1.7684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8174    1.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4113    2.1971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  1  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
  7 23  1  1  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END

     RDKit          3D

 45 49  0  0  0  0  0  0  0  0999 V2000
    3.5954   -2.5006    1.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2806   -1.0705    2.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6867   -0.5046    3.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992   -0.3122    1.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987   -0.7492   -0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1614   -2.1033   -0.4949 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3420    0.3210   -0.7576 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0140    0.1902   -1.3852 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7239   -1.0389   -1.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5909   -2.3298   -1.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6248   -3.0821   -1.2664 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4374   -2.3114   -0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6360   -2.4883    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2147   -1.4205    0.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6538   -0.1611    0.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4468    0.0184    0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8948   -1.0443   -0.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7590    1.3073    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7300    1.4296   -0.9750 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3371    2.3883   -0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0993    3.0985   -1.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2009    3.3769    0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2604    1.4117    0.1833 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0656    1.0654    1.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3492    1.8248    2.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4063   -2.8087    2.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7028   -3.1358    2.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9288   -2.7642    0.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7143   -2.8711   -0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1122    0.7231   -1.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1922    0.3254   -2.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2145   -2.7560   -2.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7925   -4.1084   -1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0679   -3.4824    0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1574   -1.5692    1.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0547    0.6930    1.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4918    2.1533   -0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3634    1.4637    1.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1707    1.9656   -1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2087    2.9490   -1.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7464    2.7041   -2.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9571    4.2046   -1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2085    3.7070    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4901    4.2708    0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1432    3.0211    1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  2  0
 17 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 24  4  1  0
 23  7  1  0
  9  8  1  0
 15 16  1  0
  9 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  7 30  1  6
  8 31  1  6
 19 39  1  6
 18 37  1  0
 18 38  1  0
 11 33  1  0
 10 32  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 21 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 22 45  1  0
M  END


  Mrv1652309022213032D          

 25 29  0  0  1  0            999 V2000
    7.3596    0.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6596    0.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6877   -0.4050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9315    0.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1897    0.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0458   -0.3659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6171    1.0403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8048    1.1843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1542    0.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0960   -0.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2953   -0.3450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8587    0.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0464    0.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7649    1.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957    1.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2754    1.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3896    0.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9259    2.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6906    2.0013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4324    2.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9958    3.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0829    2.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0050    1.7684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8174    1.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4113    2.1971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  1  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
  7 23  1  1  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0154273

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=C(O)[C@H]2[C@@H]3[C@@H](CC4=C5C(NC=C35)=CC=C4)C(C)(C)N2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17-/m1/s1

> <INCHI_KEY>
SZINUGQCTHLQAZ-OAUYIBNBSA-N

> <FORMULA>
C20H20N2O3

> <MOLECULAR_WEIGHT>
336.391

> <EXACT_MASS>
336.147392512

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.95198306062933

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,9R)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0^{2,9}.0^{3,7}.0^{15,18}]octadeca-1(17),4,11(18),12,14-pentaen-6-one

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
1.7741740986666668

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.03923979533419

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.842312874289381

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6087122679224303

> <JCHEM_POLAR_SURFACE_AREA>
73.4

> <JCHEM_REFRACTIVITY>
94.6425

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,9R)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0^{2,9}.0^{3,7}.0^{15,18}]octadeca-1(17),4,11(18),12,14-pentaen-6-one

> <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      13.738   1.598   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.431   0.783   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.484  -0.756   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.072   1.507   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.687   0.833   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.419  -0.683   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.619   1.942   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.102   2.211   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.888   1.264   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.779  -0.273   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.285  -0.644   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.470   0.663   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.953   0.931   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.428   2.379   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.419   3.558   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.247   3.367   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.460   1.842   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.462   4.314   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.889   3.736   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.274   4.410   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.459   5.716   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.488   5.357   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       9.343   3.301   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      10.859   3.032   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.968   4.101   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   24                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   23                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16    9   12                                                  
CONECT   18   16   19                                                       
CONECT   19   18    8   20                                                  
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20    7   24                                                  
CONECT   24   23    4   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
Iso-a-cyclopiazonate	Generator
Iso-a-cyclopiazonic acid	Generator
Iso-alpha-cyclopiazonate	Generator
Iso-α-cyclopiazonate	Generator
Iso-α-cyclopiazonic acid	Generator

Chemical Formula

C₂₀H₂₀N₂O₃

Average Mass

336.3910 Da

Monoisotopic Mass

336.14739 Da

IUPAC Name

(2R,3R,9R)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0^{2,9}.0^{3,7}.0^{15,18}]octadeca-1(17),4,11(18),12,14-pentaen-6-one

Traditional Name

(2R,3R,9R)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0^{2,9}.0^{3,7}.0^{15,18}]octadeca-1(17),4,11(18),12,14-pentaen-6-one

CAS Registry Number

Not Available

SMILES

CC(=O)C1=C(O)[C@H]2[C@@H]3[C@@H](CC4=C5C(NC=C35)=CC=C4)C(C)(C)N2C1=O

InChI Identifier

InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17-/m1/s1

InChI Key

SZINUGQCTHLQAZ-OAUYIBNBSA-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 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Isoindole or derivatives
Isoindoline
Pyrrolizine
Benzenoid
Heteroaromatic compound
Vinylogous acid
Tertiary carboxylic acid amide
Pyrroline
Pyrrolidine
Pyrrole
Lactam
Ketone
Carboxamide group
Azacycle
Enol
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	2.47	ALOGPS
logP	1.77	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.84	ChemAxon
pKa (Strongest Basic)	-0.61	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	73.4 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.64 m³·mol⁻¹	ChemAxon
Polarizability	34.95 Å³	ChemAxon
Number of Rings	5	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

78441354

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54732361

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sun K, Li Y, Guo L, Wang Y, Liu P, Zhu W: Indole diterpenoids and isocoumarin from the fungus, Aspergillus flavus, isolated from the prawn, Penaeus vannamei. Mar Drugs. 2014 Jun 30;12(7):3970-81. doi: 10.3390/md12073970. [PubMed:24983640 ]
Zhu H, Chen C, Wang J, Li XN, Wei G, Guo Y, Yao G, Luo Z, Zhang J, Xue Y, Zhang Y: Penicamedine A, a Highly Oxygenated Hexacyclic Indole Alkaloid from Penicillium camemberti. Chem Biodivers. 2015 Oct;12(10):1547-53. doi: 10.1002/cbdv.201400412. [PubMed:26460559 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one (NP0154273)

MOL for NP0154273 ((2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one)

3D MOL for NP0154273 ((2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one)

3D SDF for NP0154273 ((2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one)

3D-SDF for NP0154273 ((2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one)

PDB for NP0154273 ((2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one)

3D PDB for NP0154273 ((2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one)

SMILES for NP0154273 ((2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one)

INCHI for NP0154273 ((2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one)

Structure for NP0154273 ((2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one)

3D Structure for NP0154273 ((2r,3r,9r)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one)