NP-MRD: Showing NP-Card for (3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione (NP0219011)

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Record Information

Version

2.0

Created at

2022-09-05 19:51:52 UTC

Updated at

2022-09-05 19:51:52 UTC

NP-MRD ID

NP0219011

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione

Description

Jadomycin B belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. Jadomycin B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione is found in Apis cerana. (3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione was first documented in 2015 (PMID: 26515616). Based on a literature review a small amount of articles have been published on jadomycin B (PMID: 35985040) (PMID: 31819261) (PMID: 28429060) (PMID: 27502190).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052221512D          

 40 45  0  0  1  0            999 V2000
    6.4852    2.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7629    1.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7469    0.8698    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4533    0.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0246    0.4712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2776    0.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1217    1.6314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7138    0.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9521   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -3.3098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -0.0357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -0.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7032   -0.3475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9732    0.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7834    0.5880    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0534    1.3675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3235   -0.0357    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1336    0.1202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0534   -0.8152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5935   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433   -0.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -3.1539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -0.3475    0.0000 N   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
  3  4  1  6  0  0  0
  5  3  1  6  0  0  0
  5  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  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  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
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 25 33  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 22 37  1  0  0  0  0
 37 38  1  0  0  0  0
 18 38  1  0  0  0  0
 38 39  2  0  0  0  0
 19 40  1  0  0  0  0
  9 40  1  0  0  0  0
  5 40  1  0  0  0  0
M  END


  Mrv1652309052221512D          

 40 45  0  0  1  0            999 V2000
    6.4852    2.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7629    1.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7469    0.8698    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4533    0.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0246    0.4712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2776    0.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1217    1.6314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7138    0.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9521   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -3.3098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -0.0357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -0.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7032   -0.3475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9732    0.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7834    0.5880    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0534    1.3675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3235   -0.0357    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1336    0.1202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0534   -0.8152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5935   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433   -0.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -3.1539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -0.3475    0.0000 N   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
  3  4  1  6  0  0  0
  5  3  1  6  0  0  0
  5  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  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  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
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 25 33  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 22 37  1  0  0  0  0
 37 38  1  0  0  0  0
 18 38  1  0  0  0  0
 38 39  2  0  0  0  0
 19 40  1  0  0  0  0
  9 40  1  0  0  0  0
  5 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219011

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@@H]1N2C(OC1=O)C1=CC(C)=CC(O)=C1C1=C2C(=O)C2=C(O[C@H]3C[C@@H](O)[C@@H](O)[C@H](C)O3)C=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H31NO9/c1-5-13(3)24-30(37)40-29-16-9-12(2)10-17(32)21(16)23-25(31(24)29)28(36)22-15(27(23)35)7-6-8-19(22)39-20-11-18(33)26(34)14(4)38-20/h6-10,13-14,18,20,24,26,29,32-34H,5,11H2,1-4H3/t13-,14-,18+,20-,24-,26-,29?/m0/s1

> <INCHI_KEY>
BSBSCJRAEMDCHC-LVOPHWFOSA-N

> <FORMULA>
C30H31NO9

> <MOLECULAR_WEIGHT>
549.576

> <EXACT_MASS>
549.199881582

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
56.64778427445385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-[(2S)-butan-2-yl]-19-{[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0^{2,6}.0^{7,12}.0^{15,20}]henicosa-1(13),7(12),8,10,15,17,19-heptaene-4,14,21-trione

> <JCHEM_LOGP>
3.838252088333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.866968477354774

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.183426894762588

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2528866875223716

> <JCHEM_POLAR_SURFACE_AREA>
142.83

> <JCHEM_REFRACTIVITY>
142.68990000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-[(2S)-butan-2-yl]-19-{[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0^{2,6}.0^{7,12}.0^{15,20}]henicosa-1(13),7(12),8,10,15,17,19-heptaene-4,14,21-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      12.106   3.907   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.757   3.163   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.728   1.624   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.046   0.828   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.379   0.880   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.985   1.533   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.694   3.045   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.932   0.409   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.677  -0.940   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.660  -2.686   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.644  -4.432   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.685  -6.178   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.709  -1.522   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.213  -0.067   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.734  -0.940   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      16.246  -0.649   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.750   0.807   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.262   1.098   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.766   2.553   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      19.270  -0.067   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      20.783   0.224   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      18.766  -1.522   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      19.775  -2.686   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      17.254  -1.813   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      10.197  -5.887   0.000  0.00  0.00           O+0
HETATM   40  N   UNK     0       9.189  -0.649   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   40                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   40                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10   18                                                  
CONECT   18   17   19   38                                                  
CONECT   19   18   20   40                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   37                                                  
CONECT   23   22   24   34                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   25                                                       
CONECT   34   23   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   22   38                                                  
CONECT   38   37   18   39                                                  
CONECT   39   38                                                            
CONECT   40   19    9    5                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₁NO₉

Average Mass

549.5760 Da

Monoisotopic Mass

549.19988 Da

IUPAC Name

(3S)-3-[(2S)-butan-2-yl]-19-{[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0^{2,6}.0^{7,12}.0^{15,20}]henicosa-1(13),7(12),8,10,15,17,19-heptaene-4,14,21-trione

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@@H]1N2C(OC1=O)C1=CC(C)=CC(O)=C1C1=C2C(=O)C2=C(O[C@H]3C[C@@H](O)[C@@H](O)[C@H](C)O3)C=CC=C2C1=O

InChI Identifier

InChI=1S/C30H31NO9/c1-5-13(3)24-30(37)40-29-16-9-12(2)10-17(32)21(16)23-25(31(24)29)28(36)22-15(27(23)35)7-6-8-19(22)39-20-11-18(33)26(34)14(4)38-20/h6-10,13-14,18,20,24,26,29,32-34H,5,11H2,1-4H3/t13-,14-,18+,20-,24-,26-,29?/m0/s1

InChI Key

BSBSCJRAEMDCHC-LVOPHWFOSA-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Phenanthridines and derivatives

Alternative Parents

Substituents

Phenanthridine
Alpha-amino acid ester
Quinoline quinone
Hexose monosaccharide
Naphthoquinone
O-glycosyl compound
Glycosyl compound
Naphthalene
Alpha-amino acid or derivatives
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Benzenoid
Oxane
Oxazolidinone
Vinylogous amide
Oxazolidine
Lactone
1,2-diol
Ketone
Secondary alcohol
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Enamine
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Alcohol
Organic oxide
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aldehyde
Organic oxygen compound
Organooxygen compound
Organopnictogen compound
Organonitrogen 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	3.84	ChemAxon
pKa (Strongest Acidic)	8.18	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	142.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	142.69 m³·mol⁻¹	ChemAxon
Polarizability	56.65 Å³	ChemAxon
Number of Rings	6	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

C00016835

Chemspider ID

58170889

KEGG Compound ID

Not Available

BioCyc ID

CPD-12934

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46173799

PDB ID

Not Available

ChEBI ID

31738

Good Scents ID

Not Available

References

General References

McKeown BT, Relja NJ, Hall SR, Gebremeskel S, MacLeod JM, Veinotte CJ, Bennett LG, Ohlund LB, Sleno L, Jakeman DL, Berman JN, Johnston B, Goralski KB: Pilot study of jadomycin B pharmacokinetics and anti-tumoral effects in zebrafish larvae and mouse breast cancer xenograft models. Can J Physiol Pharmacol. 2022 Aug 19. doi: 10.1139/cjpp-2022-0152. [PubMed:35985040 ]
Wang W, Li S, Li Z, Zhang J, Fan K, Tan G, Ai G, Lam SM, Shui G, Yang Z, Lu H, Jin P, Li Y, Chen X, Xia X, Liu X, Dannelly HK, Yang C, Yang Y, Zhang S, Alterovitz G, Xiang W, Zhang L: Harnessing the intracellular triacylglycerols for titer improvement of polyketides in Streptomyces. Nat Biotechnol. 2020 Jan;38(1):76-83. doi: 10.1038/s41587-019-0335-4. Epub 2019 Dec 9. [PubMed:31819261 ]
Li L, Pan G, Zhu X, Fan K, Gao W, Ai G, Ren J, Shi M, Olano C, Salas JA, Yang K: Engineered jadomycin analogues with altered sugar moieties revealing JadS as a substrate flexible O-glycosyltransferase. Appl Microbiol Biotechnol. 2017 Jul;101(13):5291-5300. doi: 10.1007/s00253-017-8256-y. Epub 2017 Apr 20. [PubMed:28429060 ]
Zhu J, Sun D, Liu W, Chen Z, Li J, Wen Y: AvaR2, a pseudo gamma-butyrolactone receptor homologue from Streptomyces avermitilis, is a pleiotropic repressor of avermectin and avenolide biosynthesis and cell growth. Mol Microbiol. 2016 Nov;102(4):562-578. doi: 10.1111/mmi.13479. Epub 2016 Aug 25. [PubMed:27502190 ]
Li S, Wang J, Li X, Yin S, Wang W, Yang K: Genome-wide identification and evaluation of constitutive promoters in streptomycetes. Microb Cell Fact. 2015 Oct 29;14:172. doi: 10.1186/s12934-015-0351-0. [PubMed:26515616 ]
LOTUS database [Link]

Showing NP-Card for (3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione (NP0219011)

MOL for NP0219011 ((3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

3D MOL for NP0219011 ((3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

3D SDF for NP0219011 ((3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

3D-SDF for NP0219011 ((3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

PDB for NP0219011 ((3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

3D PDB for NP0219011 ((3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

SMILES for NP0219011 ((3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

INCHI for NP0219011 ((3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

Structure for NP0219011 ((3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)

3D Structure for NP0219011 ((3s)-3-[(2s)-butan-2-yl]-19-{[(2s,4r,5r,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.0²,⁶.0⁷,¹².0¹⁵,²⁰]henicosa-1(13),7,9,11,15,17,19-heptaene-4,14,21-trione)