NP-MRD: Showing NP-Card for (4z,7s,9r)-12-bromo-6-hydroxy-4-[hydroxy(3h-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one (NP0227698)

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Record Information

Version

2.0

Created at

2022-09-06 07:06:39 UTC

Updated at

2022-09-06 07:06:39 UTC

NP-MRD ID

NP0227698

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4z,7s,9r)-12-bromo-6-hydroxy-4-[hydroxy(3h-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

Description

11-Bromo-17-hydroxyroquefortine C 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. (4z,7s,9r)-12-bromo-6-hydroxy-4-[hydroxy(3h-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one is found in Penicillium chrysogenum. Based on a literature review very few articles have been published on 11-bromo-17-hydroxyroquefortine C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062209062D          

 31 35  0  0  1  0            999 V2000
    0.7890    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2150    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.7859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9143    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4162    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2884   -0.3960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3538   -1.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9181   -2.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5200   -2.8014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7098   -2.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6071   -1.8276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5337    1.4917    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  1  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
  9 11  2  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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  8 22  1  1  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
  6 31  1  0  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -4.2475   -1.3233   -1.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1383   -1.3087   -0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0660   -0.3435   -0.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6202    0.8287   -1.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1091   -1.0518   -1.9203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3438    0.0488    0.3106 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8212   -1.1850    1.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415   -0.7347    1.5074 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4818   -1.7524    1.9211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0785   -2.6735    2.8774 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -1.8510    1.4505 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2067   -0.9634    0.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4205   -1.1221   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1958   -2.1505    0.5549 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9560   -0.2827   -1.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1007    0.4760   -0.8550 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3740    1.0822   -2.0152 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4523    0.7302   -2.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5934   -0.1005   -2.3299 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983    0.0570   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6969    0.8887   -0.9010 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9770    0.1518    0.4515 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1716    0.9730    0.0741 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3488    2.1164    0.8989 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260    2.0802    1.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655    3.0308    2.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5219    2.7748    2.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1841    1.5997    2.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9402    1.2223    3.0576 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5157    0.6844    1.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2452    0.8690    1.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0682   -2.0352   -1.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3506   -0.6056   -2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0092   -2.0047    0.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9498    1.7046   -1.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543    0.4992   -2.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6338    1.1228   -1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1160   -2.1337   -1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4663   -0.9490   -2.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0896   -0.6314   -1.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8197   -2.0877    0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961   -1.3571    1.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569   -0.0639    2.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9701   -3.6658    2.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2991   -2.9922   -0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6753    0.5647    0.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4295    1.0824   -3.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7620   -0.5589   -2.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1530    1.2442   -0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3719    2.8566    1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7674    3.9653    2.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0339    3.5152    3.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0393   -0.2405    1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  5  1  0
  3  2  1  0
  2  1  2  3
  6  3  1  6
  6  7  1  0
  7  8  1  0
  8 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 22 20  1  0
 20 21  2  0
 20 12  1  0
 12 11  1  0
 11  9  2  0
  9 10  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 23  6  1  0
 31 25  1  0
 19 15  1  0
 31  6  1  0
  9  8  1  0
  4 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  5 40  1  0
  2 34  1  0
  1 32  1  0
  1 33  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  1
 23 49  1  6
 24 50  1  0
 26 51  1  0
 27 52  1  0
 30 53  1  0
 10 44  1  0
 14 45  1  0
 16 46  1  0
 18 47  1  0
 19 48  1  0
M  END


  Mrv1652309062209062D          

 31 35  0  0  1  0            999 V2000
    0.7890    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2150    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.7859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9143    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4162    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2884   -0.3960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3538   -1.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9181   -2.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5200   -2.8014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7098   -2.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6071   -1.8276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5337    1.4917    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  1  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
  9 11  2  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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  8 22  1  1  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
  6 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227698

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)[C@@]12C[C@@H]3N(C1NC1=CC=C(Br)C=C21)C(=O)\C(N=C3O)=C(\O)C1=CN=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22BrN5O3/c1-4-21(2,3)22-8-15-18(30)27-16(17(29)14-9-24-10-25-14)19(31)28(15)20(22)26-13-6-5-11(23)7-12(13)22/h4-7,9-10,15,20,26,29H,1,8H2,2-3H3,(H,24,25)(H,27,30)/b17-16-/t15-,20?,22+/m0/s1

> <INCHI_KEY>
UMCGQJQCISUBIM-IWLGAPBKSA-N

> <FORMULA>
C22H22BrN5O3

> <MOLECULAR_WEIGHT>
484.354

> <EXACT_MASS>
483.090603

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
45.80602553723395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4Z,7S,9R)-12-bromo-6-hydroxy-4-[hydroxy(1H-imidazol-5-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

> <JCHEM_LOGP>
1.2594278157234604

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
6.022129904769356

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.894997428706073

> <JCHEM_PKA_STRONGEST_BASIC>
7.576875039639643

> <JCHEM_POLAR_SURFACE_AREA>
113.83999999999999

> <JCHEM_REFRACTIVITY>
121.53739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4Z,7S,9R)-12-bromo-6-hydroxy-4-[hydroxy(3H-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.473   4.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.007   4.255   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.662   2.861   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.268   2.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.056   3.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.316   1.467   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.440   2.520   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.789   1.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.244   2.282   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.533   3.795   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       9.409   1.275   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.119  -0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.284  -1.244   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.738  -0.739   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.994  -2.757   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.047  -3.880   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      10.304  -5.229   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       8.792  -4.940   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       8.600  -3.411   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       7.664  -0.742   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.374  -2.255   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       6.499   0.265   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       4.971   0.073   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       3.848  -0.980   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       2.499  -0.237   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.044  -0.742   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.121   0.265   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.169   1.777   0.000  0.00  0.00           C+0
HETATM   29 Br   UNK     0      -0.996   2.784   0.000  0.00  0.00          Br+0
HETATM   30  C   UNK     0       1.624   2.282   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.788   1.275   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   23   31                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20   12   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    8   23                                                  
CONECT   23   22    6   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25    6                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂BrN₅O₃

Average Mass

484.3540 Da

Monoisotopic Mass

483.09060 Da

IUPAC Name

(4Z,7S,9R)-12-bromo-6-hydroxy-4-[hydroxy(1H-imidazol-5-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

Traditional Name

(4Z,7S,9R)-12-bromo-6-hydroxy-4-[hydroxy(3H-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)[C@@]12C[C@@H]3N(C1NC1=CC=C(Br)C=C21)C(=O)\C(N=C3O)=C(\O)C1=CN=CN1

InChI Identifier

InChI=1S/C22H22BrN5O3/c1-4-21(2,3)22-8-15-18(30)27-16(17(29)14-9-24-10-25-14)19(31)28(15)20(22)26-13-6-5-11(23)7-12(13)22/h4-7,9-10,15,20,26,29H,1,8H2,2-3H3,(H,24,25)(H,27,30)/b17-16-/t15-,20?,22+/m0/s1

InChI Key

UMCGQJQCISUBIM-IWLGAPBKSA-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 chrysogenum	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
Alpha-amino acid or derivatives
Dihydroindole
Indole
Secondary aliphatic/aromatic amine
Benzenoid
Aryl halide
Aryl bromide
Heteroaromatic compound
Vinylogous acid
Cyclic carboximidic acid
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Imidazole
Azole
Lactam
Carboxamide group
Amino acid or derivatives
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Carbonyl group
Amine
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	1.26	ChemAxon
pKa (Strongest Acidic)	2.89	ChemAxon
pKa (Strongest Basic)	7.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	113.84 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	121.54 m³·mol⁻¹	ChemAxon
Polarizability	45.81 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

Chemspider ID

78441907

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585429

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4z,7s,9r)-12-bromo-6-hydroxy-4-[hydroxy(3h-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one (NP0227698)

MOL for NP0227698 ((4z,7s,9r)-12-bromo-6-hydroxy-4-[hydroxy(3h-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D MOL for NP0227698 ((4z,7s,9r)-12-bromo-6-hydroxy-4-[hydroxy(3h-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D SDF for NP0227698 ((4z,7s,9r)-12-bromo-6-hydroxy-4-[hydroxy(3h-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D-SDF for NP0227698 ((4z,7s,9r)-12-bromo-6-hydroxy-4-[hydroxy(3h-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

PDB for NP0227698 ((4z,7s,9r)-12-bromo-6-hydroxy-4-[hydroxy(3h-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D PDB for NP0227698 ((4z,7s,9r)-12-bromo-6-hydroxy-4-[hydroxy(3h-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

SMILES for NP0227698 ((4z,7s,9r)-12-bromo-6-hydroxy-4-[hydroxy(3h-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

INCHI for NP0227698 ((4z,7s,9r)-12-bromo-6-hydroxy-4-[hydroxy(3h-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

Structure for NP0227698 ((4z,7s,9r)-12-bromo-6-hydroxy-4-[hydroxy(3h-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D Structure for NP0227698 ((4z,7s,9r)-12-bromo-6-hydroxy-4-[hydroxy(3h-imidazol-4-yl)methylidene]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)