NP-MRD: Showing NP-Card for (-)-Mirabamide B (NP0076867)

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Record Information

Version

2.0

Created at

2022-04-28 22:03:31 UTC

Updated at

2022-04-28 22:03:31 UTC

NP-MRD ID

NP0076867

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Mirabamide B

Description

(2S,3S,4R)-N-[(3R,4R,7R,13S,16S,19R,24S,25aS)-24-chloro-5,8,11,17-tetrahydroxy-16-[(1R)-1-hydroxyethyl]-19-[(R)-methoxy(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)methyl]-7-(methoxymethyl)-13,15-dimethyl-1,14,20-trioxo-3-(propan-2-yl)-1H,3H,4H,7H,10H,13H,14H,15H,16H,19H,20H,22H,23H,24H,25H,25aH-pyrido[2,1-c]1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-4-yl]-2-{[(2Z)-2-{[(2S,3R)-1,3-dihydroxy-2-[(1-hydroxy-2-{[(2S,3R,4Z,6E,8S)-1,2,3-trihydroxy-2,6,8-trimethyldeca-4,6-dien-1-ylidene]amino}ethylidene)amino]butylidene]amino}-1-hydroxybut-2-en-1-ylidene]amino}-3,4-dimethylpentanediimidic acid belongs to the class of organic compounds known as cyclic glycodepsipeptides. These are peptidomimetic containing a glycodepisipeptide backbone that lies in a cyclic moiety. (-)-Mirabamide B is found in Siliquariaspongia mirabilis. Based on a literature review very few articles have been published on (2S,3S,4R)-N-[(3R,4R,7R,13S,16S,19R,24S,25aS)-24-chloro-5,8,11,17-tetrahydroxy-16-[(1R)-1-hydroxyethyl]-19-[(R)-methoxy(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)methyl]-7-(methoxymethyl)-13,15-dimethyl-1,14,20-trioxo-3-(propan-2-yl)-1H,3H,4H,7H,10H,13H,14H,15H,16H,19H,20H,22H,23H,24H,25H,25aH-pyrido[2,1-c]1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-4-yl]-2-{[(2Z)-2-{[(2S,3R)-1,3-dihydroxy-2-[(1-hydroxy-2-{[(2S,3R,4Z,6E,8S)-1,2,3-trihydroxy-2,6,8-trimethyldeca-4,6-dien-1-ylidene]amino}ethylidene)amino]butylidene]amino}-1-hydroxybut-2-en-1-ylidene]amino}-3,4-dimethylpentanediimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200032D          

110113  0  0  1  0            999 V2000
    2.4856   -7.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  7  9  1  0  0  0  0
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 26 27  1  0  0  0  0
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  4 32  1  0  0  0  0
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 30 34  1  6  0  0  0
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M  END

     RDKit          3D

221224  0  0  0  0  0  0  0  0999 V2000
    9.4375   -2.9907   -0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1172   -3.4719   -0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0191   -2.7756   -0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1638   -0.2955   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1572   -0.3356    0.9595 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2277    1.0484   -0.9104 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3106    1.8035   -0.2809 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2599    2.3762    0.9887 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2122    2.2378    1.6675 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5411    3.2405    0.7081 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3418    2.1550    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0545    1.0003    0.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4674    2.3545   -0.6205 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.0351    1.7077   -1.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7100    3.6756   -0.8919 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7559    1.6009   -0.1670 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.3445    0.3145    0.1379 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304292200032D          

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 66 68  1  0  0  0  0
 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  2  0  0  0  0
 71 72  1  0  0  0  0
 72 73  2  0  0  0  0
 73 74  1  0  0  0  0
 74 75  1  0  0  0  0
 75 76  1  0  0  0  0
 74 77  1  1  0  0  0
 72 78  1  0  0  0  0
 69 79  1  1  0  0  0
 68 80  1  1  0  0  0
 68 81  1  1  0  0  0
 25 82  1  1  0  0  0
 82 83  1  0  0  0  0
 83 84  1  0  0  0  0
 17 85  1  6  0  0  0
 14 86  1  0  0  0  0
 13 87  1  1  0  0  0
 87 88  1  0  0  0  0
 87 89  1  1  0  0  0
  9 90  1  1  0  0  0
 90 91  1  6  0  0  0
 91 92  1  0  0  0  0
 90 93  1  0  0  0  0
 93 94  2  0  0  0  0
 94 95  1  0  0  0  0
 95 96  2  0  0  0  0
 96 97  1  0  0  0  0
 97 98  2  0  0  0  0
 93 98  1  0  0  0  0
 96 99  1  0  0  0  0
100 99  1  6  0  0  0
100101  1  0  0  0  0
101102  1  0  0  0  0
102103  1  0  0  0  0
103104  1  0  0  0  0
104105  1  0  0  0  0
100105  1  0  0  0  0
104106  1  1  0  0  0
103107  1  6  0  0  0
102108  1  1  0  0  0
101109  1  1  0  0  0
  2110  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0076867

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)\C=C(/C)\C=C/[C@@H](O)[C@](C)(O)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N\C(=C/C)C(=O)N[C@@H]([C@@H](C)[C@@H](C)C(N)=O)C(=O)N[C@@H]1[C@H](OC(=O)[C@@H]2C[C@@H](Cl)CCN2C(=O)[C@H](NC(=O)[C@H]([C@@H](C)O)N(C)C(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](COC)NC1=O)[C@H](OC)C1=CC=C(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)C=C1)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C72H111ClN12O25/c1-17-33(5)27-34(6)19-24-47(88)72(13,105)71(104)76-30-49(90)80-51(38(10)86)64(98)78-44(18-2)62(96)81-50(35(7)36(8)60(74)94)63(97)82-52-58(32(3)4)110-69(103)46-28-42(73)25-26-85(46)68(102)53(59(107-16)41-20-22-43(23-21-41)109-70-57(93)56(92)55(91)40(12)108-70)83-66(100)54(39(11)87)84(14)67(101)37(9)77-48(89)29-75-61(95)45(31-106-15)79-65(52)99/h18-24,27,32-33,35-40,42,45-47,50-59,70,86-88,91-93,105H,17,25-26,28-31H2,1-16H3,(H2,74,94)(H,75,95)(H,76,104)(H,77,89)(H,78,98)(H,79,99)(H,80,90)(H,81,96)(H,82,97)(H,83,100)/b24-19-,34-27+,44-18-/t33-,35-,36+,37-,38+,39+,40-,42-,45+,46-,47+,50-,51-,52+,53+,54-,55-,56+,57+,58+,59+,70-,72-/m0/s1

> <INCHI_KEY>
UHQCAXFLMDVFDC-MROVCFGVSA-N

> <FORMULA>
C72H111ClN12O25

> <MOLECULAR_WEIGHT>
1580.19

> <EXACT_MASS>
1578.7471848

> <JCHEM_ACCEPTOR_COUNT>
24

> <JCHEM_ATOM_COUNT>
221

> <JCHEM_AVERAGE_POLARIZABILITY>
161.8798070005985

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
17

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4R)-N-[(3R,4R,7R,13S,16S,19R,24S,25aS)-24-chloro-16-[(1R)-1-hydroxyethyl]-19-[(R)-methoxy(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)methyl]-7-(methoxymethyl)-13,15-dimethyl-1,5,8,11,14,17,20-heptaoxo-3-(propan-2-yl)-tetracosahydropyrido[2,1-c]1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-4-yl]-2-[(2Z)-2-[(2S,3R)-2-{2-[(2S,3R,4Z,6E,8S)-2,3-dihydroxy-2,6,8-trimethyldeca-4,6-dienamido]acetamido}-3-hydroxybutanamido]but-2-enamido]-3,4-dimethylpentanediamide

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
-5.0343980406666615

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.434087750095925

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.07445886649055

> <JCHEM_PKA_STRONGEST_BASIC>
-3.953910056102509

> <JCHEM_POLAR_SURFACE_AREA>
550.44

> <JCHEM_REFRACTIVITY>
391.6544

> <JCHEM_ROTATABLE_BOND_COUNT>
28

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R)-N-[(3R,4R,7R,13S,16S,19R,24S,25aS)-24-chloro-16-[(1R)-1-hydroxyethyl]-3-isopropyl-19-[(R)-methoxy(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)methyl]-7-(methoxymethyl)-13,15-dimethyl-1,5,8,11,14,17,20-heptaoxo-hexadecahydropyrido[2,1-c]1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-4-yl]-2-[(2Z)-2-[(2S,3R)-2-{2-[(2S,3R,4Z,6E,8S)-2,3-dihydroxy-2,6,8-trimethyldeca-4,6-dienamido]acetamido}-3-hydroxybutanamido]but-2-enamido]-3,4-dimethylpentanediamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.640 -13.627   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.609 -12.483   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.103 -12.803   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.627 -14.268   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.658 -15.412   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.164 -15.092   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.182 -16.877   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.675 -17.197   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.212 -18.021   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.736 -19.486   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.230 -19.806   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.754 -21.271   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.199 -18.661   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -1.307 -18.982   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -2.337 -17.837   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.861 -16.373   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.844 -18.157   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -4.874 -17.013   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -6.380 -17.333   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.856 -18.798   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -7.411 -16.189   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -6.935 -14.724   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -7.966 -13.580   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -9.472 -13.900   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -7.490 -12.115   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      -5.983 -11.795   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      -4.953 -12.939   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.429 -14.404   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.446 -12.619   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.416 -13.764   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.910 -13.443   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.121 -14.588   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.355 -16.052   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.940 -12.299   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.434 -11.979   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.101 -10.767   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0      -2.971 -11.154   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.335 -10.780   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   45  N   UNK     0      -8.002  -6.160   0.000  0.00  0.00           N+0
HETATM   46  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   48  N   UNK     0      -2.667  -7.700   0.000  0.00  0.00           N+0
HETATM   49  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -0.000  -6.160   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   54  N   UNK     0       1.334  -8.470   0.000  0.00  0.00           N+0
HETATM   55  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       4.627 -11.417   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       2.667 -10.780   0.000  0.00  0.00           O+0
HETATM   61  N   UNK     0       5.335  -7.700   0.000  0.00  0.00           N+0
HETATM   62  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   65  N   UNK     0       8.002  -6.160   0.000  0.00  0.00           N+0
HETATM   66  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0       9.336  -3.850   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      13.337  -6.160   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      14.670  -8.470   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      16.004 -10.780   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      14.670 -13.090   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   79  O   UNK     0      12.003  -8.470   0.000  0.00  0.00           O+0
HETATM   80  C   UNK     0      11.439  -4.826   0.000  0.00  0.00           C+0
HETATM   81  O   UNK     0       9.899  -7.494   0.000  0.00  0.00           O+0
HETATM   82  C   UNK     0      -8.520 -10.971   0.000  0.00  0.00           C+0
HETATM   83  O   UNK     0      -8.044  -9.506   0.000  0.00  0.00           O+0
HETATM   84  C   UNK     0      -9.075  -8.361   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      -4.320 -19.622   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      -1.783 -20.446   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0      -0.276 -20.126   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0      -0.115 -21.658   0.000  0.00  0.00           C+0
HETATM   89  O   UNK     0      -1.307 -21.271   0.000  0.00  0.00           O+0
HETATM   90  C   UNK     0       4.719 -17.701   0.000  0.00  0.00           C+0
HETATM   91  O   UNK     0       5.194 -16.236   0.000  0.00  0.00           O+0
HETATM   92  C   UNK     0       6.701 -15.916   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0       5.749 -18.845   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0       7.255 -18.525   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0       8.286 -19.670   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0       7.810 -21.134   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0       6.304 -21.454   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0       5.273 -20.310   0.000  0.00  0.00           C+0
HETATM   99  O   UNK     0       8.840 -22.279   0.000  0.00  0.00           O+0
HETATM  100  C   UNK     0      10.347 -21.959   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      11.377 -23.103   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      12.884 -22.783   0.000  0.00  0.00           C+0
HETATM  103  C   UNK     0      13.359 -21.318   0.000  0.00  0.00           C+0
HETATM  104  C   UNK     0      12.329 -20.174   0.000  0.00  0.00           C+0
HETATM  105  O   UNK     0      10.823 -20.494   0.000  0.00  0.00           O+0
HETATM  106  C   UNK     0      12.805 -18.709   0.000  0.00  0.00           C+0
HETATM  107  O   UNK     0      14.866 -20.998   0.000  0.00  0.00           O+0
HETATM  108  O   UNK     0      13.914 -23.927   0.000  0.00  0.00           O+0
HETATM  109  O   UNK     0      10.901 -24.568   0.000  0.00  0.00           O+0
HETATM  110 Cl   UNK     0       5.074 -12.007   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3  110                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   32                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   90                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   87                                                  
CONECT   14   13   15   86                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   85                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   82                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   37                                                  
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31    4   33                                                  
CONECT   33   32                                                            
CONECT   34   30   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   29   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   48                                                  
CONECT   41   40   42   47                                                  
CONECT   42   41   43   46                                                  
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   42                                                            
CONECT   47   41                                                            
CONECT   48   40   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52   54                                                  
CONECT   52   51   53                                                       
CONECT   53   52                                                            
CONECT   54   51   55                                                       
CONECT   55   54   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   58   61                                                  
CONECT   58   57   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58                                                            
CONECT   61   57   62                                                       
CONECT   62   61   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66   69   80   81                                             
CONECT   69   68   70   79                                                  
CONECT   70   69   71                                                       
CONECT   71   70   72                                                       
CONECT   72   71   73   78                                                  
CONECT   73   72   74                                                       
CONECT   74   73   75   77                                                  
CONECT   75   74   76                                                       
CONECT   76   75                                                            
CONECT   77   74                                                            
CONECT   78   72                                                            
CONECT   79   69                                                            
CONECT   80   68                                                            
CONECT   81   68                                                            
CONECT   82   25   83                                                       
CONECT   83   82   84                                                       
CONECT   84   83                                                            
CONECT   85   17                                                            
CONECT   86   14                                                            
CONECT   87   13   88   89                                                  
CONECT   88   87                                                            
CONECT   89   87                                                            
CONECT   90    9   91   93                                                  
CONECT   91   90   92                                                       
CONECT   92   91                                                            
CONECT   93   90   94   98                                                  
CONECT   94   93   95                                                       
CONECT   95   94   96                                                       
CONECT   96   95   97   99                                                  
CONECT   97   96   98                                                       
CONECT   98   97   93                                                       
CONECT   99   96  100                                                       
CONECT  100   99  101  105                                                  
CONECT  101  100  102  109                                                  
CONECT  102  101  103  108                                                  
CONECT  103  102  104  107                                                  
CONECT  104  103  105  106                                                  
CONECT  105  104  100                                                       
CONECT  106  104                                                            
CONECT  107  103                                                            
CONECT  108  102                                                            
CONECT  109  101                                                            
CONECT  110    2                                                            
MASTER        0    0    0    0    0    0    0    0  110    0  226    0
END

View in JSmol

Synonyms

Value

Source

(2S,3S,4R)-N-[(3R,4R,7R,13S,16S,19R,24S,25AS)-24-chloro-5,8,11,17-tetrahydroxy-16-[(1R)-1-hydroxyethyl]-19-[(R)-methoxy(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)methyl]-7-(methoxymethyl)-13,15-dimethyl-1,14,20-trioxo-3-(propan-2-yl)-1H,3H,4H,7H,10H,13H,14H,15H,16H,19H,20H,22H,23H,24H,25H,25ah-pyrido[2,1-c]1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-4-yl]-2-{[(2Z)-2-{[(2S,3R)-1,3-dihydroxy-2-[(1-hydroxy-2-{[(2S,3R,4Z,6E,8S)-1,2,3-trihydroxy-2,6,8-trimethyldeca-4,6-dien-1-ylidene]amino}ethylidene)amino]butylidene]amino}-1-hydroxybut-2-en-1-ylidene]amino}-3,4-dimethylpentanediimidate

Generator

Chemical Formula

C₇₂H₁₁₁ClN₁₂O₂₅

Average Mass

1580.1900 Da

Monoisotopic Mass

1578.74718 Da

IUPAC Name

(2S,3S,4R)-N-[(3R,4R,7R,13S,16S,19R,24S,25aS)-24-chloro-16-[(1R)-1-hydroxyethyl]-19-[(R)-methoxy(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)methyl]-7-(methoxymethyl)-13,15-dimethyl-1,5,8,11,14,17,20-heptaoxo-3-(propan-2-yl)-tetracosahydropyrido[2,1-c]1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-4-yl]-2-[(2Z)-2-[(2S,3R)-2-{2-[(2S,3R,4Z,6E,8S)-2,3-dihydroxy-2,6,8-trimethyldeca-4,6-dienamido]acetamido}-3-hydroxybutanamido]but-2-enamido]-3,4-dimethylpentanediamide

Traditional Name

(2S,3S,4R)-N-[(3R,4R,7R,13S,16S,19R,24S,25aS)-24-chloro-16-[(1R)-1-hydroxyethyl]-3-isopropyl-19-[(R)-methoxy(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)methyl]-7-(methoxymethyl)-13,15-dimethyl-1,5,8,11,14,17,20-heptaoxo-hexadecahydropyrido[2,1-c]1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-4-yl]-2-[(2Z)-2-[(2S,3R)-2-{2-[(2S,3R,4Z,6E,8S)-2,3-dihydroxy-2,6,8-trimethyldeca-4,6-dienamido]acetamido}-3-hydroxybutanamido]but-2-enamido]-3,4-dimethylpentanediamide

CAS Registry Number

Not Available

SMILES

CC[C@H](C)\C=C(/C)\C=C/[C@@H](O)[C@](C)(O)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N\C(=C/C)C(=O)N[C@@H]([C@@H](C)[C@@H](C)C(N)=O)C(=O)N[C@@H]1[C@H](OC(=O)[C@@H]2C[C@@H](Cl)CCN2C(=O)[C@H](NC(=O)[C@H]([C@@H](C)O)N(C)C(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](COC)NC1=O)[C@H](OC)C1=CC=C(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)C=C1)C(C)C

InChI Identifier

InChI=1S/C72H111ClN12O25/c1-17-33(5)27-34(6)19-24-47(88)72(13,105)71(104)76-30-49(90)80-51(38(10)86)64(98)78-44(18-2)62(96)81-50(35(7)36(8)60(74)94)63(97)82-52-58(32(3)4)110-69(103)46-28-42(73)25-26-85(46)68(102)53(59(107-16)41-20-22-43(23-21-41)109-70-57(93)56(92)55(91)40(12)108-70)83-66(100)54(39(11)87)84(14)67(101)37(9)77-48(89)29-75-61(95)45(31-106-15)79-65(52)99/h18-24,27,32-33,35-40,42,45-47,50-59,70,86-88,91-93,105H,17,25-26,28-31H2,1-16H3,(H2,74,94)(H,75,95)(H,76,104)(H,77,89)(H,78,98)(H,79,99)(H,80,90)(H,81,96)(H,82,97)(H,83,100)/b24-19-,34-27+,44-18-/t33-,35-,36+,37-,38+,39+,40-,42-,45+,46-,47+,50-,51-,52+,53+,54-,55-,56+,57+,58+,59+,70-,72-/m0/s1

InChI Key

UHQCAXFLMDVFDC-MROVCFGVSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Siliquariaspongia mirabilis	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic glycodepsipeptides. These are peptidomimetic containing a glycodepisipeptide backbone that lies in a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic glycodepsipeptides

Alternative Parents

Substituents

Cyclic glycodepsipeptide
Phenolic glycoside
Macrolide lactam
Macrolactam
Alpha-amino acid ester
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Alpha-amino acid or derivatives
Benzylether
Phenoxy compound
Phenol ether
Benzenoid
Piperidine
Oxane
Monosaccharide
Monocyclic benzene moiety
Cyclic carboximidic acid
Tertiary carboxylic acid amide
Tertiary alcohol
Secondary alcohol
Lactone
Lactam
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Alcohol
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	1.8	ALOGPS
logP	-5	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	11.07	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	24	ChemAxon
Hydrogen Donor Count	17	ChemAxon
Polar Surface Area	550.44 Å²	ChemAxon
Rotatable Bond Count	28	ChemAxon
Refractivity	391.65 m³·mol⁻¹	ChemAxon
Polarizability	161.88 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163106166

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Mirabamide B (NP0076867)

MOL for NP0076867 ((-)-Mirabamide B)

3D MOL for NP0076867 ((-)-Mirabamide B)

3D SDF for NP0076867 ((-)-Mirabamide B)

3D-SDF for NP0076867 ((-)-Mirabamide B)

PDB for NP0076867 ((-)-Mirabamide B)

3D PDB for NP0076867 ((-)-Mirabamide B)

SMILES for NP0076867 ((-)-Mirabamide B)

INCHI for NP0076867 ((-)-Mirabamide B)

Structure for NP0076867 ((-)-Mirabamide B)

3D Structure for NP0076867 ((-)-Mirabamide B)