MiMeDB: Showing metabocard for Okaramine B (MMDBc0001331)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 19:35:15 UTC

Update Date

2025-10-07 16:04:27 UTC

Metabolite ID

MMDBc0001331

Metabolite Identification

Common Name

Okaramine B

Description

Okaramine B is a member of the indole alkaloid chemical class, primarily derived from the fermentation products of fungi such as Penicillium simplicissimum. Its biosynthesis involves a gene cluster that exhibits distinct transcriptional patterns influenced by fermentation conditions, as highlighted in studies that reveal key genes associated with its regulation (PMID:38396642 ). Notably, tryptophan metabolism has been shown to correlate significantly with the yields of Okaramine B, indicating its biochemical pathways are intricately linked to amino acid metabolism (PMID:38396642 ). Okaramine B has been detected in various soil environments, including the rhizosphere of hairy vetch and soybean crops, suggesting its ecological presence and potential roles in soil microbiomes (PMID:32153648 ). Additionally, this compound has been noted for its biological activity, activating the IscaGluCl1 receptor in a concentration-dependent manner, which positions it as a candidate for developing new acaricides (PMID:29957333 ). However, the precise binding mechanisms of Okaramine B on insect glutamate-gated chloride channels remain poorly understood, particularly in relation to mutations that affect sensitivity (PMID:28825521 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142121352D          

 47 54  0  0  1  0            999 V2000
    3.6802   -0.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1021    2.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7094    1.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3281   -1.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2598   -2.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4823    1.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8004   -1.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6242   -0.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5559   -1.2954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149   -1.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1356   -1.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378   -0.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6465   -0.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3808   -1.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1721    2.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3741    2.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8794    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593   -0.6034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2262   -0.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6774    0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580   -0.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9816    0.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673   -1.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1671    0.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0937    1.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5807   -0.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    0.9876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1621    1.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8844    1.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5595   -1.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    0.2189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5756    0.9400    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0906   -0.3037    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8997    0.8340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9578    1.3025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7909   -1.0723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7849    0.1420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0263   -0.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9528    2.3183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8139    0.7415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841    1.7118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3063    1.6818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2841    3.0414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8754    2.6720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674   -0.7291    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3580   -1.2606    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1976    0.2933    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 16 15  2  0  0  0  0
 18  1  1  6  0  0  0
 19 11  2  0  0  0  0
 20 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21 12  2  0  0  0  0
 22 13  2  0  0  0  0
 22 19  1  0  0  0  0
 23 14  2  0  0  0  0
 23 21  1  0  0  0  0
 24 17  2  0  0  0  0
 25 20  2  0  0  0  0
 26 24  1  0  0  0  0
 29  2  1  0  0  0  0
 29  3  1  0  0  0  0
 29 15  1  0  0  0  0
 29 25  1  0  0  0  0
 30  4  1  0  0  0  0
 30  5  1  0  0  0  0
 30 18  1  0  0  0  0
 31 21  1  0  0  0  0
 31 27  1  0  0  0  0
 32 27  1  0  0  0  0
 32 28  1  0  0  0  0
 33 18  1  0  0  0  0
 33 31  1  0  0  0  0
 34 22  1  0  0  0  0
 34 25  1  0  0  0  0
 35 16  1  0  0  0  0
 35 24  1  0  0  0  0
 35 28  1  0  0  0  0
 36 23  1  0  0  0  0
 36 30  1  0  0  0  0
 33 36  1  6  0  0  0
 37 26  1  0  0  0  0
 37 32  1  0  0  0  0
 37 33  1  0  0  0  0
 38 26  2  0  0  0  0
 39 28  2  0  0  0  0
 31 40  1  1  0  0  0
 32 41  1  1  0  0  0
 42  6  1  0  0  0  0
 27 42  1  1  0  0  0
 43 15  1  0  0  0  0
 44 16  1  0  0  0  0
 45 17  1  0  0  0  0
 18 46  1  1  0  0  0
 27 47  1  1  0  0  0
M  END


  Mrv1652305142121352D          

 47 54  0  0  1  0            999 V2000
    3.6802   -0.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1021    2.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7094    1.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3281   -1.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2598   -2.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4823    1.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8004   -1.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6242   -0.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5559   -1.2954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149   -1.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1356   -1.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378   -0.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6465   -0.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3808   -1.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1721    2.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3741    2.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8794    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593   -0.6034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2262   -0.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6774    0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580   -0.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9816    0.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673   -1.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1671    0.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0937    1.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5807   -0.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    0.9876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1621    1.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8844    1.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5595   -1.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    0.2189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5756    0.9400    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0906   -0.3037    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8997    0.8340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9578    1.3025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7909   -1.0723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7849    0.1420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0263   -0.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9528    2.3183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8139    0.7415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841    1.7118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3063    1.6818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2841    3.0414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8754    2.6720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674   -0.7291    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3580   -1.2606    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1976    0.2933    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 16 15  2  0  0  0  0
 18  1  1  6  0  0  0
 19 11  2  0  0  0  0
 20 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21 12  2  0  0  0  0
 22 13  2  0  0  0  0
 22 19  1  0  0  0  0
 23 14  2  0  0  0  0
 23 21  1  0  0  0  0
 24 17  2  0  0  0  0
 25 20  2  0  0  0  0
 26 24  1  0  0  0  0
 29  2  1  0  0  0  0
 29  3  1  0  0  0  0
 29 15  1  0  0  0  0
 29 25  1  0  0  0  0
 30  4  1  0  0  0  0
 30  5  1  0  0  0  0
 30 18  1  0  0  0  0
 31 21  1  0  0  0  0
 31 27  1  0  0  0  0
 32 27  1  0  0  0  0
 32 28  1  0  0  0  0
 33 18  1  0  0  0  0
 33 31  1  0  0  0  0
 34 22  1  0  0  0  0
 34 25  1  0  0  0  0
 35 16  1  0  0  0  0
 35 24  1  0  0  0  0
 35 28  1  0  0  0  0
 36 23  1  0  0  0  0
 36 30  1  0  0  0  0
 33 36  1  6  0  0  0
 37 26  1  0  0  0  0
 37 32  1  0  0  0  0
 37 33  1  0  0  0  0
 38 26  2  0  0  0  0
 39 28  2  0  0  0  0
 31 40  1  1  0  0  0
 32 41  1  1  0  0  0
 42  6  1  0  0  0  0
 27 42  1  1  0  0  0
 43 15  1  0  0  0  0
 44 16  1  0  0  0  0
 45 17  1  0  0  0  0
 18 46  1  1  0  0  0
 27 47  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0001331

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C1=C([H])\C(C)(C)C2=C(\C([H])=C3/N1C(=O)[C@]1(O)N(C3=O)[C@]34N(C5=CC=CC=C5[C@]3(O)[C@]1([H])OC)C(C)(C)[C@@]4([H])C)C1=CC=CC=C1N2

> <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                                 14-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-21         0                                  
HETATM    1  C   UNK     0       6.870  -0.973   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.391   4.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.524   3.366   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.213  -3.121   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.218  -3.996   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.900   3.067   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.694  -3.037   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.165  -1.100   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.104  -2.418   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.775  -2.589   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.453  -2.125   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.070  -0.017   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.273  -0.887   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.711  -2.996   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.655   4.152   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.165   3.761   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.108   0.165   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.337  -1.126   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.622  -0.595   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.598   0.555   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.415  -0.423   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.032   0.024   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.806  -1.913   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.779   0.942   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.375   1.885   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.684  -0.141   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.270   1.843   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.903   2.838   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.984   3.375   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.778  -2.561   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.711   0.409   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.808   1.755   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.903  -0.567   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      12.879   1.557   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0       7.388   2.431   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0       3.343  -2.002   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0       5.199   0.265   0.000  0.00  0.00           N+0
HETATM   38  O   UNK     0       7.516  -1.437   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       5.512   4.327   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       1.519   1.384   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       4.264   3.195   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       2.439   3.139   0.000  0.00  0.00           O+0
HETATM   43  H   UNK     0       9.864   5.677   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       7.234   4.988   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       8.899  -1.361   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       6.268  -2.353   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.102   0.547   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   29                                                            
CONECT    3   29                                                            
CONECT    4   30                                                            
CONECT    5   30                                                            
CONECT    6   42                                                            
CONECT    7    9   11                                                       
CONECT    8   10   12                                                       
CONECT    9    7   13                                                       
CONECT   10    8   14                                                       
CONECT   11    7   19                                                       
CONECT   12    8   21                                                       
CONECT   13    9   22                                                       
CONECT   14   10   23                                                       
CONECT   15   16   29   43                                                  
CONECT   16   15   35   44                                                  
CONECT   17   20   24   45                                                  
CONECT   18    1   30   33   46                                             
CONECT   19   11   20   22                                                  
CONECT   20   17   19   25                                                  
CONECT   21   12   23   31                                                  
CONECT   22   13   19   34                                                  
CONECT   23   14   21   36                                                  
CONECT   24   17   26   35                                                  
CONECT   25   20   29   34                                                  
CONECT   26   24   37   38                                                  
CONECT   27   31   32   42   47                                             
CONECT   28   32   35   39                                                  
CONECT   29    2    3   15   25                                             
CONECT   30    4    5   18   36                                             
CONECT   31   21   27   33   40                                             
CONECT   32   27   28   37   41                                             
CONECT   33   18   31   36   37                                             
CONECT   34   22   25                                                       
CONECT   35   16   24   28                                                  
CONECT   36   23   30   33                                                  
CONECT   37   26   32   33                                                  
CONECT   38   26                                                            
CONECT   39   28                                                            
CONECT   40   31                                                            
CONECT   41   32                                                            
CONECT   42    6   27                                                       
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   27                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  108    0
END

Synonyms

Not Available

Molecular Formula

C₃₃H₃₄N₄O₅

Average Mass

566.658

Monoisotopic Mass

566.252920211

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

[H]\C1=C([H])\C(C)(C)C2=C(\C([H])=C3/N1C(=O)[C@]1(O)N(C3=O)[C@]34N(C5=CC=CC=C5[C@]3(O)[C@]1([H])OC)C(C)(C)[C@@]4([H])C)C1=CC=CC=C1N2

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

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
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

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-23	86.8
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-23	36.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	702.5
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	703.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	739.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	265.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3562.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	88.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	316.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	558.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	102.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	174.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	231.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	8.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	136.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	161.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	502.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1934.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1415.8

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Okaramine B_TMS_1	CO[C@@H]1[C@]2(O[Si](C)(C)C)C(=O)N3/C=C/C(C)(C)C4=C(/C=C\3C(=O)N2[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O)C1=CC=CC=C1[NH]4	standard non polar	2025-10-23	1145.86
Gas Chromatography	Okaramine B_TMS_2	CO[C@@H]1[C@]2(O)C(=O)N3/C=C/C(C)(C)C4=C(/C=C\3C(=O)N2[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O[Si](C)(C)C)C1=CC=CC=C1[NH]4	standard non polar	2025-10-23	2734.42
Gas Chromatography	Okaramine B_TMS_3	CO[C@@H]1[C@]2(O)C(=O)N3/C=C/C(C)(C)C4=C(/C=C\3C(=O)N2[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O)C1=CC=CC=C1N4[Si](C)(C)C	standard non polar	2025-10-23	939.676
Gas Chromatography	Okaramine B_TMS_4	CO[C@@H]1[C@]2(O[Si](C)(C)C)C(=O)N3/C=C/C(C)(C)C4=C(/C=C\3C(=O)N2[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O[Si](C)(C)C)C1=CC=CC=C1[NH]4	standard non polar	2025-10-23	1399.32
Gas Chromatography	Okaramine B_TMS_5	CO[C@@H]1[C@]2(O[Si](C)(C)C)C(=O)N3/C=C/C(C)(C)C4=C(/C=C\3C(=O)N2[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O)C1=CC=CC=C1N4[Si](C)(C)C	standard non polar	2025-10-23	629.976
Gas Chromatography	Okaramine B_TMS_6	CO[C@@H]1[C@]2(O)C(=O)N3/C=C/C(C)(C)C4=C(/C=C\3C(=O)N2[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O[Si](C)(C)C)C1=CC=CC=C1N4[Si](C)(C)C	standard non polar	2025-10-23	2048.74
Gas Chromatography	Okaramine B_TMS_7	CO[C@@H]1[C@]2(O[Si](C)(C)C)C(=O)N3/C=C/C(C)(C)C4=C(/C=C\3C(=O)N2[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O[Si](C)(C)C)C1=CC=CC=C1N4[Si](C)(C)C	standard non polar	2025-10-23	3998.45
Gas Chromatography	Okaramine B_TMS_1	CO[C@@H]1[C@]2(O[Si](C)(C)C)C(=O)N3/C=C/C(C)(C)C4=C(/C=C\3C(=O)N2[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O)C1=CC=CC=C1[NH]4	standard polar	2025-10-23	3148.93
Gas Chromatography	Okaramine B_TMS_2	CO[C@@H]1[C@]2(O)C(=O)N3/C=C/C(C)(C)C4=C(/C=C\3C(=O)N2[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O[Si](C)(C)C)C1=CC=CC=C1[NH]4	standard polar	2025-10-23	1127.25
Gas Chromatography	Okaramine B_TMS_3	CO[C@@H]1[C@]2(O)C(=O)N3/C=C/C(C)(C)C4=C(/C=C\3C(=O)N2[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O)C1=CC=CC=C1N4[Si](C)(C)C	standard polar	2025-10-23	2459.07
Gas Chromatography	Okaramine B_TMS_4	CO[C@@H]1[C@]2(O[Si](C)(C)C)C(=O)N3/C=C/C(C)(C)C4=C(/C=C\3C(=O)N2[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O[Si](C)(C)C)C1=CC=CC=C1[NH]4	standard polar	2025-10-23	1664.43
Gas Chromatography	Okaramine B_TMS_5	CO[C@@H]1[C@]2(O[Si](C)(C)C)C(=O)N3/C=C/C(C)(C)C4=C(/C=C\3C(=O)N2[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O)C1=CC=CC=C1N4[Si](C)(C)C	standard polar	2025-10-23	2638.62
Gas Chromatography	Okaramine B_TMS_6	CO[C@@H]1[C@]2(O)C(=O)N3/C=C/C(C)(C)C4=C(/C=C\3C(=O)N2[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O[Si](C)(C)C)C1=CC=CC=C1N4[Si](C)(C)C	standard polar	2025-10-23	955.108
Gas Chromatography	Okaramine B_TMS_7	CO[C@@H]1[C@]2(O[Si](C)(C)C)C(=O)N3/C=C/C(C)(C)C4=C(/C=C\3C(=O)N2[C@]23[C@H](C)C(C)(C)N2C2=CC=CC=C2[C@]13O[Si](C)(C)C)C1=CC=CC=C1N4[Si](C)(C)C	standard polar	2025-10-23	2349.33

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Okaramine B (MMDBc0001331)

MOL for #<Metabolite:0x00007f9ac91f4e40>

3D MOL for #<Metabolite:0x00007f9ac91f4e40>

3D SDF for #<Metabolite:0x00007f9ac91f4e40>

3D-SDF for #<Metabolite:0x00007f9ac91f4e40>

PDB for #<Metabolite:0x00007f9ac91f4e40>

3D PDB for #<Metabolite:0x00007f9ac91f4e40>

SMILES for #<Metabolite:0x00007f9ac91f4e40>

INCHI for #<Metabolite:0x00007f9ac91f4e40>

Structure for #<Metabolite:0x00007f9ac91f4e40>

3D Structure for #<Metabolite:0x00007f9ac91f4e40>