NP-MRD: Showing NP-Card for (1z,4s,5r,14r,15s,16s,19z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0³,¹⁶.0⁴,⁷.0⁴,¹⁴.0⁸,¹³.0²²,³⁰.0²⁴,²⁹]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione (NP0160039)

truetrue

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truetrue

Record Information

Version

1.0

Created at

2022-09-02 17:53:58 UTC

Updated at

2022-09-02 17:53:58 UTC

NP-MRD ID

NP0160039

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1z,4s,5r,14r,15s,16s,19z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0³,¹⁶.0⁴,⁷.0⁴,¹⁴.0⁸,¹³.0²²,³⁰.0²⁴,²⁹]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione

Description

Okaramine B belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (1z,4s,5r,14r,15s,16s,19z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0³,¹⁶.0⁴,⁷.0⁴,¹⁴.0⁸,¹³.0²²,³⁰.0²⁴,²⁹]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione is found in Penicillium simplicissimum. It was first documented in 2014 (PMID: 25155752). Based on a literature review a small amount of articles have been published on Okaramine B (PMID: 32153648) (PMID: 29957333) (PMID: 28825521) (PMID: 27153748).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022219542D          

 42 49  0  0  1  0            999 V2000
    0.3875    4.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1938    4.1716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    3.4265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5756    3.3789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2908    4.2034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1621    3.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1374    4.8351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9578    3.7415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3741    4.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1721    4.6630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8844    4.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1308    5.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7401    4.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0937    3.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8997    3.2729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9816    2.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6465    1.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5559    1.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8004    0.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1356    1.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2262    2.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6774    2.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5031    2.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8435    1.4874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0906    2.1353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.6402    1.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1265    0.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7909    1.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673    1.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4149    1.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4523    2.6579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7776    3.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
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  4  5  1  1  0  0  0
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 40 41  1  0  0  0  0
  3 41  1  0  0  0  0
 28 41  1  0  0  0  0
 41 42  1  1  0  0  0
M  END

     RDKit          3D

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   -1.2854   -1.0549   -2.9746 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6178   -1.6964   -1.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7660   -1.7313   -0.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4259    0.7596   -1.9662 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -4.3758   -1.8055   -1.2342 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022219542D          

 42 49  0  0  1  0            999 V2000
    0.3875    4.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1938    4.1716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    3.4265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5756    3.3789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2908    4.2034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1621    3.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1374    4.8351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9578    3.7415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3741    4.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1721    4.6630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8004    0.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1356    1.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2262    2.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6774    2.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8794    2.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1671    2.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    2.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8435    1.4874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7849    2.5809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0906    2.1353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8593    1.8356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6402    1.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5595    1.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1265    0.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2031    0.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7909    1.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673    1.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3808    0.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149    1.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6242    1.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378    2.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    2.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    2.6579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7776    3.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 14 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 28 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
 40 41  1  0  0  0  0
  3 41  1  0  0  0  0
 28 41  1  0  0  0  0
 41 42  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0160039

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@@]2(O)N(C(=O)\C3=C\C4=C(NC5=CC=CC=C45)C(C)(C)\C=C/N3C2=O)[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O

> <INCHI_IDENTIFIER>
InChI=1S/C33H34N4O5/c1-18-30(4,5)36-23-14-10-8-12-21(23)31(40)27(42-6)32(41)28(39)35-16-15-29(2,3)25-20(19-11-7-9-13-22(19)34-25)17-24(35)26(38)37(32)33(18,31)36/h7-18,27,34,40-41H,1-6H3/b16-15-,24-17-/t18-,27+,31+,32+,33+/m1/s1

> <INCHI_KEY>
PNJDFZNVNWQTFD-KTJJPEJQSA-N

> <FORMULA>
C33H34N4O5

> <MOLECULAR_WEIGHT>
566.658

> <EXACT_MASS>
566.252920211

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
60.160653965940845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,5R,14R,15S,16S,19Z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0^{3,16}.0^{4,7}.0^{4,14}.0^{8,13}.0^{22,30}.0^{24,29}]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
4.1671950916666685

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.02355731934397

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.075234785192945

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2872140811502667

> <JCHEM_POLAR_SURFACE_AREA>
109.34000000000002

> <JCHEM_REFRACTIVITY>
158.03810000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5R,14R,15S,16S,19Z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0^{3,16}.0^{4,7}.0^{4,14}.0^{8,13}.0^{22,30}.0^{24,29}]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-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       0.723   8.467   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.228   7.787   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.270   6.396   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.808   6.307   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.276   7.846   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.903   7.391   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.856   9.025   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       7.388   6.984   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       8.165   8.314   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.655   8.704   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.984   7.927   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.444   9.508   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.582   8.297   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.375   6.438   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      12.879   6.109   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      13.032   4.577   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.273   3.665   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.104   2.135   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.694   1.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.453   2.427   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.622   3.958   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.598   5.108   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.108   4.717   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.779   5.494   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.539   4.574   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.174   2.777   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0       5.199   4.818   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       3.903   3.986   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.337   3.426   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.795   3.614   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.778   1.992   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.836   0.751   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.113   0.495   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       3.343   2.551   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       1.806   2.640   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.711   1.557   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.775   1.963   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.165   3.453   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.070   4.536   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.415   4.129   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.711   4.961   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.452   5.929   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   41                                                  
CONECT    4    3    5    6   27                                             
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   24                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   14   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    8   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    4   28                                                  
CONECT   28   27   29   34   41                                             
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   28   35                                                  
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   35   41                                                  
CONECT   41   40    3   28   42                                             
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₄N₄O₅

Average Mass

566.6580 Da

Monoisotopic Mass

566.25292 Da

IUPAC Name

(4S,5R,14R,15S,16S,19Z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0^{3,16}.0^{4,7}.0^{4,14}.0^{8,13}.0^{22,30}.0^{24,29}]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@@]2(O)N(C(=O)\C3=C\C4=C(NC5=CC=CC=C45)C(C)(C)\C=C/N3C2=O)[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O

InChI Identifier

InChI=1S/C33H34N4O5/c1-18-30(4,5)36-23-14-10-8-12-21(23)31(40)27(42-6)32(41)28(39)35-16-15-29(2,3)25-20(19-11-7-9-13-22(19)34-25)17-24(35)26(38)37(32)33(18,31)36/h7-18,27,34,40-41H,1-6H3/b16-15-,24-17-/t18-,27+,31+,32+,33+/m1/s1

InChI Key

PNJDFZNVNWQTFD-KTJJPEJQSA-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 simplicissimum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Benzazepine
Alpha-amino acid or derivatives
Indole
Dioxopiperazine
2,5-dioxopiperazine
Dialkylarylamine
N-alkylpiperazine
Azepine
1,4-diazinane
Benzenoid
Piperazine
Heteroaromatic compound
Tertiary carboxylic acid amide
Tertiary alcohol
Pyrrole
Pyrrolidine
Carboxamide group
Lactam
Azetidine
Alkanolamine
Azacycle
Dialkyl ether
Carboxylic acid derivative
Ether
Alcohol
Organonitrogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Amine
Organic oxygen compound
Organic nitrogen 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	4.06	ALOGPS
logP	4.17	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	10.08	ChemAxon
pKa (Strongest Basic)	-0.29	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.34 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	158.04 m³·mol⁻¹	ChemAxon
Polarizability	60.16 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00011255

Chemspider ID

23326454

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14312904

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sakurai N, Mardani-Korrani H, Nakayasu M, Matsuda K, Ochiai K, Kobayashi M, Tahara Y, Onodera T, Aoki Y, Motobayashi T, Komatsuzaki M, Ihara M, Shibata D, Fujii Y, Sugiyama A: Metabolome Analysis Identified Okaramines in the Soybean Rhizosphere as a Legacy of Hairy Vetch. Front Genet. 2020 Feb 24;11:114. doi: 10.3389/fgene.2020.00114. eCollection 2020. [PubMed:32153648 ]
Furutani S, Ihara M, Lees K, Buckingham SD, Partridge FA, David JA, Patel R, Warchal S, Mellor IR, Matsuda K, Sattelle DB: The fungal alkaloid Okaramine-B activates an L-glutamate-gated chloride channel from Ixodes scapularis, a tick vector of Lyme disease. Int J Parasitol Drugs Drug Resist. 2018 Aug;8(2):350-360. doi: 10.1016/j.ijpddr.2018.06.001. Epub 2018 Jun 4. [PubMed:29957333 ]
Furutani S, Okuhara D, Hashimoto A, Ihara M, Kai K, Hayashi H, Sattelle DB, Matsuda K: An L319F mutation in transmembrane region 3 (TM3) selectively reduces sensitivity to okaramine B of the Bombyx mori l-glutamate-gated chloride channel. Biosci Biotechnol Biochem. 2017 Oct;81(10):1861-1867. doi: 10.1080/09168451.2017.1359487. Epub 2017 Aug 21. [PubMed:28825521 ]
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LOTUS database [Link]

truetrue

Showing NP-Card for (1z,4s,5r,14r,15s,16s,19z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0³,¹⁶.0⁴,⁷.0⁴,¹⁴.0⁸,¹³.0²²,³⁰.0²⁴,²⁹]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione (NP0160039)

MOL for NP0160039 ((1z,4s,5r,14r,15s,16s,19z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0³,¹⁶.0⁴,⁷.0⁴,¹⁴.0⁸,¹³.0²²,³⁰.0²⁴,²⁹]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione)

3D MOL for NP0160039 ((1z,4s,5r,14r,15s,16s,19z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0³,¹⁶.0⁴,⁷.0⁴,¹⁴.0⁸,¹³.0²²,³⁰.0²⁴,²⁹]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione)

3D SDF for NP0160039 ((1z,4s,5r,14r,15s,16s,19z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0³,¹⁶.0⁴,⁷.0⁴,¹⁴.0⁸,¹³.0²²,³⁰.0²⁴,²⁹]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione)

3D-SDF for NP0160039 ((1z,4s,5r,14r,15s,16s,19z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0³,¹⁶.0⁴,⁷.0⁴,¹⁴.0⁸,¹³.0²²,³⁰.0²⁴,²⁹]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione)

PDB for NP0160039 ((1z,4s,5r,14r,15s,16s,19z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0³,¹⁶.0⁴,⁷.0⁴,¹⁴.0⁸,¹³.0²²,³⁰.0²⁴,²⁹]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione)

3D PDB for NP0160039 ((1z,4s,5r,14r,15s,16s,19z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0³,¹⁶.0⁴,⁷.0⁴,¹⁴.0⁸,¹³.0²²,³⁰.0²⁴,²⁹]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione)

SMILES for NP0160039 ((1z,4s,5r,14r,15s,16s,19z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0³,¹⁶.0⁴,⁷.0⁴,¹⁴.0⁸,¹³.0²²,³⁰.0²⁴,²⁹]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione)

INCHI for NP0160039 ((1z,4s,5r,14r,15s,16s,19z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0³,¹⁶.0⁴,⁷.0⁴,¹⁴.0⁸,¹³.0²²,³⁰.0²⁴,²⁹]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione)

Structure for NP0160039 ((1z,4s,5r,14r,15s,16s,19z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0³,¹⁶.0⁴,⁷.0⁴,¹⁴.0⁸,¹³.0²²,³⁰.0²⁴,²⁹]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione)

3D Structure for NP0160039 ((1z,4s,5r,14r,15s,16s,19z)-14,16-dihydroxy-15-methoxy-5,6,6,21,21-pentamethyl-3,7,18,23-tetraazaoctacyclo[16.13.0.0³,¹⁶.0⁴,⁷.0⁴,¹⁴.0⁸,¹³.0²²,³⁰.0²⁴,²⁹]hentriaconta-1(31),8,10,12,19,22(30),24,26,28-nonaene-2,17-dione)