NP-MRD: Showing NP-Card for Ustiloxin F (NP0023758)

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Record Information

Version

2.0

Created at

2021-01-06 08:48:16 UTC

Updated at

2021-07-15 17:42:36 UTC

NP-MRD ID

NP0023758

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ustiloxin F

Provided By

NPAtlas

Description

Ustiloxin F is found in Ustilaginoidea virens. Ustiloxin F was first documented in 1998 (PMID: 9630863). Based on a literature review very few articles have been published on 2-({[(3R,4S,7S,10S,11R)-3-ethyl-6,9,11,15-tetrahydroxy-3,7-dimethyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]Hexadeca-1(15),5,8,12(16),13-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120443D          

 63 64  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242120443D          

 63 64  0  0  0  0            999 V2000
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   -1.9102    1.1200   -1.0277 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3264    2.2627   -1.9809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9354    0.3231   -1.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4385    0.3869   -1.8816 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    0.2366   -0.8361 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6113    1.0994   -1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7003    1.5259   -2.3775 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6256    1.4870   -0.2917 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7455    2.3337   -0.7175 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6567    2.5920    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3640    2.0846    1.5390 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7878    3.3530    0.3162 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0004   -2.8919    1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6445   -3.3650    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0016   -0.8170   -0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0208   -0.9631    1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6455   -1.1838   -2.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8277   -2.7002   -1.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2185   -2.3433   -2.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2390   -0.2436    1.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0788   -2.3032    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0648   -3.9053   -0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1564   -4.6494   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2114   -0.6832    2.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8641   -0.1393    3.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6872    1.7510    2.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1523    2.1138    0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2189    1.2699    0.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9306    1.2167    2.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6722   -0.2791    1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5635    2.3386    0.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8049    0.5035   -0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201    2.6555   -2.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951    1.8967   -2.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546    3.0933   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8482    0.5738   -2.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615    0.6325    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6087    1.2046    0.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2915    1.8573   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    3.2981   -1.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1403    3.8303    1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 26  3  1  0  0  0  0
 11  6  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  2 37  1  0  0  0  0
  2 38  1  0  0  0  0
  4 39  1  0  0  0  0
  4 40  1  0  0  0  0
  4 41  1  0  0  0  0
  7 42  1  0  0  0  0
  9 43  1  0  0  0  0
 10 44  1  0  0  0  0
 12 45  1  0  0  0  0
 13 46  1  1  0  0  0
 14 47  1  0  0  0  0
 15 48  1  1  0  0  0
 16 49  1  0  0  0  0
 17 50  1  0  0  0  0
 17 51  1  0  0  0  0
 17 52  1  0  0  0  0
 20 53  1  0  0  0  0
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 25 58  1  0  0  0  0
 26 59  1  1  0  0  0
 29 60  1  0  0  0  0
 30 61  1  0  0  0  0
 30 62  1  0  0  0  0
 33 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])N([H])C(=O)[C@@]1([H])N([H])C(=O)[C@@]([H])(N([H])C(=O)[C@@]([H])(N([H])C([H])([H])[H])[C@]([H])(O[H])C2=C([H])C([H])=C(O[H])C(O[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])[H])=C2[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H30N4O8/c1-5-21(3)17(20(32)23-9-14(27)28)25-18(30)10(2)24-19(31)15(22-4)16(29)11-6-7-12(26)13(8-11)33-21/h6-8,10,15-17,22,26,29H,5,9H2,1-4H3,(H,23,32)(H,24,31)(H,25,30)(H,27,28)/t10-,15-,16+,17+,21+/m0/s1

> <INCHI_KEY>
XAJYTGHEDODUTC-KILRJQPKSA-N

> <FORMULA>
C21H30N4O8

> <MOLECULAR_WEIGHT>
466.491

> <EXACT_MASS>
466.206363942

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.2997654304766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(3R,4S,7S,10S,11R)-3-ethyl-11,15-dihydroxy-3,7-dimethyl-10-(methylamino)-6,9-dioxo-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),12,14-trien-4-yl]formamido}acetic acid

> <ALOGPS_LOGP>
-0.37

> <JCHEM_LOGP>
-3.8309084114207317

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.757537102387193

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.20533992147724

> <JCHEM_PKA_STRONGEST_BASIC>
7.689966637855935

> <JCHEM_POLAR_SURFACE_AREA>
186.31999999999996

> <JCHEM_REFRACTIVITY>
113.80419999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[(3R,4S,7S,10S,11R)-3-ethyl-11,15-dihydroxy-3,7-dimethyl-10-(methylamino)-6,9-dioxo-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),12,14-trien-4-yl]formamido}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 64  0  0  0  0  0  0  0  0999 V2000
    3.5495   -2.7692    0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1501   -1.2827    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8565   -1.1968   -0.6769 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1372   -1.8511   -2.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9512   -2.0228   -0.0203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3557   -1.9472    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9248   -1.0275    1.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552   -1.1382    1.5809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9976   -2.1841    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4737   -3.1084    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1273   -2.9534   -0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6096   -3.9338   -1.0327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1305   -0.2701    2.4182 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8436   -0.1557    3.7439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2849    1.1516    1.8561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2119    1.2096    0.8035 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5629    0.8386    1.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9757    1.7127    1.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2687    2.2175    2.4136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4327    1.7565    0.1420 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9102    1.1200   -1.0277 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3264    2.2627   -1.9809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9354    0.3231   -1.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4958   -0.5886   -2.5266 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4385    0.3869   -1.8816 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    0.2366   -0.8361 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6113    1.0994   -1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7003    1.5259   -2.3775 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6256    1.4870   -0.2917 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7455    2.3337   -0.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6567    2.5920    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3640    2.0846    1.5390 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7878    3.3530    0.3162 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3460   -3.0301   -0.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0004   -2.8919    1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6445   -3.3650    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0016   -0.8170   -0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0208   -0.9631    1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6455   -1.1838   -2.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8277   -2.7002   -1.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2185   -2.3433   -2.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2390   -0.2436    1.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0788   -2.3032    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0648   -3.9053   -0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1564   -4.6494   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2114   -0.6832    2.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8641   -0.1393    3.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6872    1.7510    2.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1523    2.1138    0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2189    1.2699    0.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9306    1.2167    2.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6722   -0.2791    1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5635    2.3386    0.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8049    0.5035   -0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201    2.6555   -2.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951    1.8967   -2.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546    3.0933   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8482    0.5738   -2.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615    0.6325    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6087    1.2046    0.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2915    1.8573   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    3.2981   -1.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1403    3.8303    1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  8 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 26  3  1  0
 11  6  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  4 39  1  0
  4 40  1  0
  4 41  1  0
  7 42  1  0
  9 43  1  0
 10 44  1  0
 12 45  1  0
 13 46  1  1
 14 47  1  0
 15 48  1  1
 16 49  1  0
 17 50  1  0
 17 51  1  0
 17 52  1  0
 20 53  1  0
 21 54  1  1
 22 55  1  0
 22 56  1  0
 22 57  1  0
 25 58  1  0
 26 59  1  1
 29 60  1  0
 30 61  1  0
 30 62  1  0
 33 63  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.550  -2.769   0.236  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.150  -1.283   0.088  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.857  -1.197  -0.677  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.137  -1.851  -2.039  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.951  -2.023  -0.020  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.356  -1.947   0.420  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.925  -1.028   1.296  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.255  -1.138   1.581  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.998  -2.184   0.984  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.474  -3.108   0.125  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.127  -2.953  -0.136  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.610  -3.934  -1.033  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.131  -0.270   2.418  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.844  -0.156   3.744  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.285   1.152   1.856  0.00  0.00           C+0
HETATM   16  N   UNK     0      -4.212   1.210   0.804  0.00  0.00           N+0
HETATM   17  C   UNK     0      -5.563   0.839   1.140  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.976   1.713   1.439  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.269   2.217   2.414  0.00  0.00           O+0
HETATM   20  N   UNK     0      -1.433   1.757   0.142  0.00  0.00           N+0
HETATM   21  C   UNK     0      -1.910   1.120  -1.028  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.326   2.263  -1.981  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.935   0.323  -1.803  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.496  -0.589  -2.527  0.00  0.00           O+0
HETATM   25  N   UNK     0       0.439   0.387  -1.882  0.00  0.00           N+0
HETATM   26  C   UNK     0       1.446   0.237  -0.836  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.611   1.099  -1.187  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.700   1.526  -2.377  0.00  0.00           O+0
HETATM   29  N   UNK     0       3.626   1.487  -0.292  0.00  0.00           N+0
HETATM   30  C   UNK     0       4.745   2.334  -0.718  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.657   2.592   0.429  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.364   2.085   1.539  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.788   3.353   0.316  0.00  0.00           O+0
HETATM   34  H   UNK     0       4.346  -3.030  -0.498  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.000  -2.892   1.222  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.644  -3.365   0.164  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.002  -0.817  -0.424  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.021  -0.963   1.147  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.646  -1.184  -2.735  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.828  -2.700  -1.827  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.218  -2.343  -2.427  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.239  -0.244   1.773  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.079  -2.303   1.195  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.065  -3.905  -0.320  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.156  -4.649  -1.428  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.211  -0.683   2.436  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.864  -0.139   3.868  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.687   1.751   2.706  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.152   2.114   0.288  0.00  0.00           H+0
HETATM   50  H   UNK     0      -6.219   1.270   0.337  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.931   1.217   2.087  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.672  -0.279   1.013  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.564   2.339   0.016  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.805   0.503  -0.895  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.420   2.656  -2.500  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.095   1.897  -2.654  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.755   3.093  -1.389  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.848   0.574  -2.857  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.062   0.633   0.076  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.609   1.205   0.690  0.00  0.00           H+0
HETATM   61  H   UNK     0       5.292   1.857  -1.562  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.361   3.298  -1.092  0.00  0.00           H+0
HETATM   63  H   UNK     0       7.140   3.830   1.155  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    1    3   37   38                                             
CONECT    3    2    4    5   26                                             
CONECT    4    3   39   40   41                                             
CONECT    5    3    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   42                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   43                                                  
CONECT   10    9   11   44                                                  
CONECT   11   10   12    6                                                  
CONECT   12   11   45                                                       
CONECT   13    8   14   15   46                                             
CONECT   14   13   47                                                       
CONECT   15   13   16   18   48                                             
CONECT   16   15   17   49                                                  
CONECT   17   16   50   51   52                                             
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   53                                                  
CONECT   21   20   22   23   54                                             
CONECT   22   21   55   56   57                                             
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   58                                                  
CONECT   26   25   27    3   59                                             
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   60                                                  
CONECT   30   29   31   61   62                                             
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   63                                                       
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    2                                                            
CONECT   38    2                                                            
CONECT   39    4                                                            
CONECT   40    4                                                            
CONECT   41    4                                                            
CONECT   42    7                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   17                                                            
CONECT   52   17                                                            
CONECT   53   20                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   22                                                            
CONECT   57   22                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   29                                                            
CONECT   61   30                                                            
CONECT   62   30                                                            
CONECT   63   33                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  128    0
END

RDKit          3D

63 64  0  0  0  0  0  0  0  0999 V2000
    3.5495   -2.7692    0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1501   -1.2827    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8565   -1.1968   -0.6769 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1372   -1.8511   -2.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9512   -2.0228   -0.0203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3557   -1.9472    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9248   -1.0275    1.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552   -1.1382    1.5809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9976   -2.1841    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4737   -3.1084    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1273   -2.9534   -0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6096   -3.9338   -1.0327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1305   -0.2701    2.4182 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8436   -0.1557    3.7439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2849    1.1516    1.8561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2119    1.2096    0.8035 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5629    0.8386    1.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9757    1.7127    1.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2687    2.2175    2.4136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4327    1.7565    0.1420 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9102    1.1200   -1.0277 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3264    2.2627   -1.9809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9354    0.3231   -1.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4958   -0.5886   -2.5266 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4385    0.3869   -1.8816 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    0.2366   -0.8361 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6113    1.0994   -1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7003    1.5259   -2.3775 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6256    1.4870   -0.2917 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7455    2.3337   -0.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6567    2.5920    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3640    2.0846    1.5390 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7878    3.3530    0.3162 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3460   -3.0301   -0.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0004   -2.8919    1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6445   -3.3650    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0016   -0.8170   -0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0208   -0.9631    1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6455   -1.1838   -2.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8277   -2.7002   -1.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2185   -2.3433   -2.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2390   -0.2436    1.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0788   -2.3032    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0648   -3.9053   -0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1564   -4.6494   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2114   -0.6832    2.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8641   -0.1393    3.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6872    1.7510    2.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1523    2.1138    0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2189    1.2699    0.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9306    1.2167    2.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6722   -0.2791    1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5635    2.3386    0.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8049    0.5035   -0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201    2.6555   -2.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951    1.8967   -2.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546    3.0933   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8482    0.5738   -2.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615    0.6325    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6087    1.2046    0.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2915    1.8573   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    3.2981   -1.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1403    3.8303    1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  8 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 26  3  1  0
 11  6  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  4 39  1  0
  4 40  1  0
  4 41  1  0
  7 42  1  0
  9 43  1  0
 10 44  1  0
 12 45  1  0
 13 46  1  1
 14 47  1  0
 15 48  1  1
 16 49  1  0
 17 50  1  0
 17 51  1  0
 17 52  1  0
 20 53  1  0
 21 54  1  1
 22 55  1  0
 22 56  1  0
 22 57  1  0
 25 58  1  0
 26 59  1  1
 29 60  1  0
 30 61  1  0
 30 62  1  0
 33 63  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-({[(3R,4S,7S,10S,11R)-3-ethyl-6,9,11,15-tetrahydroxy-3,7-dimethyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(15),5,8,12(16),13-pentaen-4-yl](hydroxy)methylidene}amino)acetate	Generator

Chemical Formula

C₂₁H₃₀N₄O₈

Average Mass

466.4910 Da

Monoisotopic Mass

466.20636 Da

IUPAC Name

2-{[(3R,4S,7S,10S,11R)-3-ethyl-11,15-dihydroxy-3,7-dimethyl-10-(methylamino)-6,9-dioxo-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),12,14-trien-4-yl]formamido}acetic acid

Traditional Name

{[(3R,4S,7S,10S,11R)-3-ethyl-11,15-dihydroxy-3,7-dimethyl-10-(methylamino)-6,9-dioxo-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),12,14-trien-4-yl]formamido}acetic acid

CAS Registry Number

Not Available

SMILES

CC[C@@]1(C)OC2=C(O)C=CC(=C2)[C@@H](O)[C@H](NC)C(=O)N[C@@H](C)C(=O)N[C@@H]1C(=O)NCC(O)=O

InChI Identifier

InChI=1S/C21H30N4O8/c1-5-21(3)17(20(32)23-9-14(27)28)25-18(30)10(2)24-19(31)15(22-4)16(29)11-6-7-12(26)13(8-11)33-21/h6-8,10,15-17,22,26,29H,5,9H2,1-4H3,(H,23,32)(H,24,31)(H,25,30)(H,27,28)/t10-,15-,16+,17+,21+/m0/s1

InChI Key

XAJYTGHEDODUTC-KILRJQPKSA-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
Ustilaginoidea virens	NPAtlas	9630863

Chemical Taxonomy

Classification

Not classified

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	-0.37	ALOGPS
logP	-3.8	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	7.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.32 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.8 m³·mol⁻¹	ChemAxon
Polarizability	46.3 Å³	ChemAxon
Number of Rings	2	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

NPAtlas ID

NPA011795

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8542712

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10367264

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Koiso Y, Morisaki N, Yamashita Y, Mitsui Y, Shirai R, Hashimoto Y, Iwasaki S: Isolation and structure of an antimitotic cyclic peptide, ustiloxin F: chemical interrelation with a homologous peptide, ustiloxin B. J Antibiot (Tokyo). 1998 Apr;51(4):418-22. doi: 10.7164/antibiotics.51.418. [PubMed:9630863 ]

Showing NP-Card for Ustiloxin F (NP0023758)

MOL for NP0023758 (Ustiloxin F)

3D MOL for NP0023758 (Ustiloxin F)

3D SDF for NP0023758 (Ustiloxin F)

3D-SDF for NP0023758 (Ustiloxin F)

PDB for NP0023758 (Ustiloxin F)

3D PDB for NP0023758 (Ustiloxin F)

SMILES for NP0023758 (Ustiloxin F)

INCHI for NP0023758 (Ustiloxin F)

Structure for NP0023758 (Ustiloxin F)

3D Structure for NP0023758 (Ustiloxin F)