NP-MRD: Showing NP-Card for (10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol (NP0266073)

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Record Information

Version

2.0

Created at

2022-09-08 10:17:25 UTC

Updated at

2022-09-08 10:17:25 UTC

NP-MRD ID

NP0266073

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol

Description

Blastmycetin F belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. (10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol is found in Streptomyces blastmyceticus. (10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol was first documented in 1994 (PMID: 8201310). Based on a literature review very few articles have been published on Blastmycetin F.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082212172D          

 29 32  0  0  1  0            999 V2000
    4.4109    3.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6519    3.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9924    3.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5524    2.3823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2880    2.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8906    2.5721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6113    1.2497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3711    0.4605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0306   -0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9311   -0.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797    0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8608    0.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4617   -0.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8113   -1.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6333   -1.4304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3390   -2.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086   -2.8157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9503   -3.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739   -2.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5141   -2.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6517   -0.4559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5501    0.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8737    0.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446    1.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918    2.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531    1.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974    0.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7488    2.1957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    2.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  4  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 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
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 12 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -4.2421   -0.7040   -1.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2587    0.0015   -0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7165    1.4444   -0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8349    0.1220    0.1621 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9362    1.0507    1.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1949    1.2262    1.9514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0045    1.7691    1.7745 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.7977    1.2986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3964    2.5427    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288    2.5622   -0.4121 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0530    0.5290    1.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634   -0.2528    0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598   -0.2079    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1061    0.6941    0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6846    1.5172    1.8068 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5332    0.7527    0.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3468    1.5859    1.2316 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6806    1.4576    0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6204    0.6450   -0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2678   -0.0303   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3448   -1.1764   -0.6007 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1907   -1.8139   -0.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9491   -2.9150   -1.7463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3301   -3.4190   -1.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3213   -2.8237   -1.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -1.7010   -0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1888   -1.2304   -0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -1.1773    0.3594 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9965   -2.1291    1.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4663   -1.7714   -1.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3379   -0.5251   -2.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1127   -0.3070   -2.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9710   -0.4540    0.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8822    1.6182   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6210    1.6817   -0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9441    2.1770   -0.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2934    0.6257   -0.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5397    0.5228    2.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615    2.5361    2.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9967    2.3202   -0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6060    3.6739    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9597    3.2461   -1.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496   -0.2029    1.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171    0.5776    2.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0481    2.4829    0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3729    1.0125    1.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7294    1.2695   -1.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3913   -0.1799   -0.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3748   -1.1050   -0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8047    0.1232   -1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2594   -1.4437   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7657   -3.3409   -2.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5037   -4.2704   -2.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2955   -3.2814   -1.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0911   -1.9631    1.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8601   -3.1836    0.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308   -1.9559    2.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4 28  1  0
 28 29  1  0
 28 26  1  0
 26 27  2  0
 27 22  1  0
 22 21  1  0
 21 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 13 12  2  0
 12 11  1  0
 11  8  1  0
  8  9  1  0
  9 10  1  0
  8  7  1  0
  7  5  2  0
  5  6  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
  5  4  1  0
 25 26  1  0
 12 27  1  0
 20 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  6
 29 55  1  0
 29 56  1  0
 29 57  1  0
 21 51  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 11 43  1  0
 11 44  1  0
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
  6 38  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
M  END


  Mrv1652309082212172D          

 29 32  0  0  1  0            999 V2000
    4.4109    3.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6519    3.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9924    3.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5524    2.3823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2880    2.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8906    2.5721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6113    1.2497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3711    0.4605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0306   -0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9311   -0.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797    0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8608    0.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4617   -0.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8113   -1.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6333   -1.4304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3390   -2.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086   -2.8157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9503   -3.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739   -2.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5141   -2.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6517   -0.4559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5501    0.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8737    0.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446    1.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918    2.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531    1.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974    0.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7488    2.1957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    2.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  4  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 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
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 12 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0266073

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1N(C)C2=C3C(NC(C(=O)C4=NCCC4)=C3C[C@@H](CO)N=C1O)=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C22H28N4O3/c1-12(2)20-22(29)24-13(11-27)10-14-18-15(6-4-8-17(18)26(20)3)25-19(14)21(28)16-7-5-9-23-16/h4,6,8,12-13,20,25,27H,5,7,9-11H2,1-3H3,(H,24,29)/t13-,20-/m0/s1

> <INCHI_KEY>
CKUVDIKBGLVWTK-RBZFPXEDSA-N

> <FORMULA>
C22H28N4O3

> <MOLECULAR_WEIGHT>
396.491

> <EXACT_MASS>
396.216140778

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.73101805824166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10S,13S)-2-(3,4-dihydro-2H-pyrrole-5-carbonyl)-13-(hydroxymethyl)-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4,6,8(15),11-pentaen-11-ol

> <JCHEM_LOGP>
2.5735260523655814

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.205250857728597

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.88960892465749

> <JCHEM_PKA_STRONGEST_BASIC>
3.2576031066695794

> <JCHEM_POLAR_SURFACE_AREA>
101.28000000000002

> <JCHEM_REFRACTIVITY>
113.1353

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(10S,13S)-2-(4,5-dihydro-3H-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4,6,8(15),11-pentaen-11-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       8.234   6.579   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.817   5.976   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.586   6.901   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.631   4.447   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.004   3.750   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.129   4.801   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       8.608   2.333   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       8.159   0.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.390  -0.066   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.205  -1.594   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.869   0.019   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.340   0.205   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.595  -1.143   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.248  -2.538   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.782  -2.670   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.366  -3.800   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.869  -5.256   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.641  -6.184   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.378  -5.303   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.826  -3.829   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.083  -0.851   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.893   0.677   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.631   1.559   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.763   3.093   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.158   3.746   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.206   2.868   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.288   1.330   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       5.131   4.099   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       4.291   5.389   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   28                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   27                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
CONECT   21   13   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   12   22                                                  
CONECT   28   26    4   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈N₄O₃

Average Mass

396.4910 Da

Monoisotopic Mass

396.21614 Da

IUPAC Name

(10S,13S)-2-(3,4-dihydro-2H-pyrrole-5-carbonyl)-13-(hydroxymethyl)-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4,6,8(15),11-pentaen-11-ol

Traditional Name

(10S,13S)-2-(4,5-dihydro-3H-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4,6,8(15),11-pentaen-11-ol

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1N(C)C2=C3C(NC(C(=O)C4=NCCC4)=C3C[C@@H](CO)N=C1O)=CC=C2

InChI Identifier

InChI=1S/C22H28N4O3/c1-12(2)20-22(29)24-13(11-27)10-14-18-15(6-4-8-17(18)26(20)3)25-19(14)21(28)16-7-5-9-23-16/h4,6,8,12-13,20,25,27H,5,7,9-11H2,1-3H3,(H,24,29)/t13-,20-/m0/s1

InChI Key

CKUVDIKBGLVWTK-RBZFPXEDSA-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
Streptomyces blastmyceticus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
3-alkylindole
Indole
Indole or derivatives
Tertiary aliphatic/aromatic amine
Aryl ketone
Dialkylarylamine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrroline
Pyrrole
Carboxamide group
Tertiary amine
Ketimine
Secondary carboxylic acid amide
Ketone
Lactam
Organoheterocyclic compound
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Primary alcohol
Alcohol
Organopnictogen compound
Organic oxygen compound
Imine
Organic oxide
Carbonyl group
Organic nitrogen compound
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	2.57	ChemAxon
pKa (Strongest Acidic)	4.89	ChemAxon
pKa (Strongest Basic)	3.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	101.28 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	113.14 m³·mol⁻¹	ChemAxon
Polarizability	43.73 Å³	ChemAxon
Number of Rings	4	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

170581

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

196953

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Irie K, Kajiyama S, Okuno S, Kondo M, Koshimizu K, Hayashi H, Arai M, Nishino H, Iwashima A: New teleocidin-related metabolites, (-)-7-geranylindolactam V and blastmycetin F, from Streptoverticillium blastmyceticum. J Nat Prod. 1994 Mar;57(3):363-8. doi: 10.1021/np50105a005. [PubMed:8201310 ]
LOTUS database [Link]

Showing NP-Card for (10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol (NP0266073)

MOL for NP0266073 ((10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D MOL for NP0266073 ((10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D SDF for NP0266073 ((10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D-SDF for NP0266073 ((10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

PDB for NP0266073 ((10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D PDB for NP0266073 ((10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

SMILES for NP0266073 ((10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

INCHI for NP0266073 ((10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

Structure for NP0266073 ((10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)

3D Structure for NP0266073 ((10s,13s)-2-(4,5-dihydro-3h-pyrrole-2-carbonyl)-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol)