NP-MRD: Showing NP-Card for fluevirosine B (NP0043148)

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Record Information

Version

1.0

Created at

2021-06-21 00:38:10 UTC

Updated at

2021-06-30 00:18:40 UTC

NP-MRD ID

NP0043148

Secondary Accession Numbers

None

Natural Product Identification

Common Name

fluevirosine B

Provided By

JEOL Database JEOL Logo

Description

(1R,2R,8R,9S)-9-[(1S,7S,8S,13R)-3-oxo-7-[(1S,8S,13R)-3-oxo-2-oxa-9-azatetracyclo[6.5.1.0¹,⁵.0⁹,¹³]Tetradeca-4,6-dien-6-yl]-2-oxa-9-azatetracyclo[6.5.1.0¹,⁵.0⁹,¹³]Tetradec-4-en-4-yl]-14-oxa-7-azatetracyclo[6.6.1.0¹,¹¹.0²,⁷]Pentadec-11-en-13-one belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen. fluevirosine B is found in Flueggea virosa. It was first documented in 2002 (PMID: 29437326). Based on a literature review a significant number of articles have been published on (1R,2R,8R,9S)-9-[(1S,7S,8S,13R)-3-oxo-7-[(1S,8S,13R)-3-oxo-2-oxa-9-azatetracyclo[6.5.1.0¹,⁵.0⁹,¹³]Tetradeca-4,6-dien-6-yl]-2-oxa-9-azatetracyclo[6.5.1.0¹,⁵.0⁹,¹³]Tetradec-4-en-4-yl]-14-oxa-7-azatetracyclo[6.6.1.0¹,¹¹.0²,⁷]Pentadec-11-en-13-one (PMID: 27466641) (PMID: 27253005) (PMID: 26389468) (PMID: 26389426).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102383D          

 87 98  0  0  0  0            999 V2000
    2.5146   -4.2624    0.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2719   -3.5195   -0.8083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8192   -2.1341   -0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6681   -1.6588   -1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1254   -0.3961   -2.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    0.7307   -1.3982 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5121    0.5060   -0.6694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9123    1.7203    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4608    1.8411    1.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8887    0.7532    2.2687 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1869    1.0585    3.0930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9058    1.4839    4.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5507    2.3531    5.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7709    2.4661    6.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0815    3.1539    7.4688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6543    1.6843    6.4323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6742    1.0058    5.1930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4773    1.3210    4.2989 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7109    0.2811    3.1906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2236   -0.8969    3.9073 N   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5616   -2.1778    3.8026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5158   -3.2308    4.3963 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0514   -2.8635    5.7934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5493   -1.4089    5.8732 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4652   -0.5083    5.3078 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5958    3.2934    1.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0711    3.8180    2.5381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1009    3.9787    0.4764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336    3.0565   -0.4815 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8591    3.1625   -0.7527 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9661    2.2064   -1.9497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1892    2.6071   -2.8065 N   0  0  2  0  0  0  0  0  0  0  0  0
    0.1746    3.6572   -3.7749 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.0084   -2.8092   -3.9374 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1047   -2.6902   -2.8927 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3416   -3.8546   -2.1281 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3129   -2.2311   -3.7463 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1449   -3.3509   -4.3689 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4184   -2.8479   -5.7728 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1138   -2.1642   -6.1341 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7262   -1.4685   -4.9001 N   0  0  1  0  0  0  0  0  0  0  0  0
    1.6045   -1.6889    0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6320    0.6670   -0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480   -0.3699   -0.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2985    0.2897   -1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8255    1.7851    2.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4681    1.1407    4.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2018    0.0784    2.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3999   -2.1818    4.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3685   -2.4294    2.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3725   -3.3530    3.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098   -4.2019    4.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8584   -3.5491    6.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2459   -3.0036    6.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7673   -1.1452    6.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4843   -1.3103    5.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5599   -0.6652    5.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    4.1887   -1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788    2.8650    0.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275    2.3152   -2.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0412    4.2448   -3.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4068    3.2253   -4.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5163    4.9179   -2.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509    5.3464   -1.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562    2.6214   -2.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073    0.5907   -4.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6696   -1.3849   -5.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1506   -3.6854   -4.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017   -2.8862   -3.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9760   -1.5641   -3.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0708   -3.5336   -3.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5874   -4.2936   -4.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2453   -2.1273   -5.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6715   -3.6587   -6.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2410   -1.4581   -6.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -2.9188   -6.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0  0  0  0
 14 15  2  0  0  0  0
 19 18  1  0  0  0  0
  8  7  1  0  0  0  0
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 25 66  1  1  0  0  0
 26 27  2  0  0  0  0
 12 13  2  0  0  0  0
 36 76  1  1  0  0  0
  9 10  1  0  0  0  0
 13 14  1  0  0  0  0
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M  END

     RDKit          3D

 87 98  0  0  0  0  0  0  0  0999 V2000
    2.5146   -4.2624    0.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2719   -3.5195   -0.8083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8192   -2.1341   -0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6681   -1.6588   -1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8439    0.7307   -1.3982 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.7109    0.2811    3.1906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2236   -0.8969    3.9073 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5616   -2.1778    3.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1138   -2.1642   -6.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7262   -1.4685   -4.9001 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6045   -1.6889    0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6320    0.6670   -0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306212102383D          

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M  END
> <DATABASE_ID>
NP0043148

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C2C(=C([H])[C@@]3([H])N4C([H])([H])C([H])([H])C([H])([H])[C@]4([H])[C@]2(OC1=O)C3([H])[H])[C@]1([H])C([H])([H])C2=C(C(=O)O[C@@]22C([H])([H])[C@]1([H])N1C([H])([H])C([H])([H])C([H])([H])[C@]21[H])[C@]1([H])C([H])([H])C2=C([H])C(=O)O[C@]22C([H])([H])[C@@]1([H])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C37H41N3O6/c41-31-12-19-11-23(27-17-35(19,44-31)28-5-1-2-8-39(27)28)33-25-14-22(26-18-37(25,46-34(33)43)30-7-4-10-40(26)30)21-13-20-16-36(24(21)15-32(42)45-36)29-6-3-9-38(20)29/h12-13,15,20,22-23,26-30H,1-11,14,16-18H2/t20-,22+,23-,26+,27-,28-,29-,30-,35-,36+,37+/m1/s1

> <INCHI_KEY>
HYWYNBKAWUIHFN-NOLXPYPPSA-N

> <FORMULA>
C37H41N3O6

> <MOLECULAR_WEIGHT>
623.75

> <EXACT_MASS>
623.299536052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
67.8449512006614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,8R,9S)-9-[(1S,7S,8S,13R)-3-oxo-7-[(1S,8S,13R)-3-oxo-2-oxa-9-azatetracyclo[6.5.1.0^{1,5}.0^{9,13}]tetradeca-4,6-dien-6-yl]-2-oxa-9-azatetracyclo[6.5.1.0^{1,5}.0^{9,13}]tetradec-4-en-4-yl]-14-oxa-7-azatetracyclo[6.6.1.0^{1,11}.0^{2,7}]pentadec-11-en-13-one

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
2.4025634686666653

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
12

> <JCHEM_PHYSIOLOGICAL_CHARGE>
3

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.675356691384007

> <JCHEM_PKA_STRONGEST_BASIC>
10.147571727390567

> <JCHEM_POLAR_SURFACE_AREA>
88.62

> <JCHEM_REFRACTIVITY>
168.40399999999988

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,8R,9S)-9-[(1S,7S,8S,13R)-3-oxo-7-[(1S,8S,13R)-3-oxo-2-oxa-9-azatetracyclo[6.5.1.0^{1,5}.0^{9,13}]tetradeca-4,6-dien-6-yl]-2-oxa-9-azatetracyclo[6.5.1.0^{1,5}.0^{9,13}]tetradec-4-en-4-yl]-14-oxa-7-azatetracyclo[6.6.1.0^{1,11}.0^{2,7}]pentadec-11-en-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 87 98  0  0  0  0  0  0  0  0999 V2000
    2.5146   -4.2624    0.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  O   UNK     0       2.515  -4.262   0.125  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.272  -3.519  -0.808  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.819  -2.134  -0.661  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.668  -1.659  -1.893  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.125  -0.396  -2.387  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.844   0.731  -1.398  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.512   0.506  -0.669  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.912   1.720   0.115  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.461   1.841   1.326  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.889   0.753   2.269  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.187   1.059   3.093  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.906   1.484   4.505  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.551   2.353   5.277  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.771   2.466   6.513  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.082   3.154   7.469  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.654   1.684   6.432  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.674   1.006   5.193  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.477   1.321   4.299  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.711   0.281   3.191  0.00  0.00           C+0
HETATM   20  N   UNK     0      -1.224  -0.897   3.907  0.00  0.00           N+0
HETATM   21  C   UNK     0      -0.562  -2.178   3.803  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.516  -3.231   4.396  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.051  -2.864   5.793  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.549  -1.409   5.873  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.465  -0.508   5.308  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.596   3.293   1.549  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.071   3.818   2.538  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.101   3.979   0.476  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.634   3.057  -0.482  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.859   3.163  -0.753  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.966   2.206  -1.950  0.00  0.00           C+0
HETATM   32  N   UNK     0      -0.189   2.607  -2.807  0.00  0.00           N+0
HETATM   33  C   UNK     0       0.175   3.657  -3.775  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.044   4.559  -3.832  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.469   4.618  -2.379  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.226   3.193  -1.891  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.962  -0.316  -3.728  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.263  -1.481  -4.664  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.008  -2.809  -3.937  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.105  -2.690  -2.893  0.00  0.00           C+0
HETATM   41  O   UNK     0       2.342  -3.855  -2.128  0.00  0.00           O+0
HETATM   42  C   UNK     0       3.313  -2.231  -3.746  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.145  -3.351  -4.369  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.418  -2.848  -5.773  0.00  0.00           C+0
HETATM   45  C   UNK     0       3.114  -2.164  -6.134  0.00  0.00           C+0
HETATM   46  N   UNK     0       2.726  -1.468  -4.900  0.00  0.00           N+0
HETATM   47  H   UNK     0       1.605  -1.689   0.292  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.632   0.667  -0.631  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.448  -0.370  -0.015  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.299   0.290  -1.404  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.158  -0.100   1.627  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.774   0.131   3.147  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.825   1.785   2.577  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.440   2.921   5.077  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.444   2.358   3.955  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.468   1.141   4.828  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.202   0.078   2.619  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.400  -2.182   4.329  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.369  -2.429   2.754  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.373  -3.353   3.720  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.010  -4.202   4.441  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.858  -3.549   6.075  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.246  -3.004   6.525  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.767  -1.145   6.914  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.484  -1.310   5.309  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.560  -0.665   5.917  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.149   4.189  -1.010  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.479   2.865   0.102  0.00  0.00           H+0
HETATM   69  H   UNK     0       1.928   2.315  -2.466  0.00  0.00           H+0
HETATM   70  H   UNK     0       1.041   4.245  -3.446  0.00  0.00           H+0
HETATM   71  H   UNK     0       0.407   3.225  -4.753  0.00  0.00           H+0
HETATM   72  H   UNK     0      -1.833   4.105  -4.444  0.00  0.00           H+0
HETATM   73  H   UNK     0      -0.815   5.548  -4.239  0.00  0.00           H+0
HETATM   74  H   UNK     0      -2.516   4.918  -2.273  0.00  0.00           H+0
HETATM   75  H   UNK     0      -0.851   5.346  -1.842  0.00  0.00           H+0
HETATM   76  H   UNK     0      -2.156   2.621  -2.000  0.00  0.00           H+0
HETATM   77  H   UNK     0       0.607   0.591  -4.206  0.00  0.00           H+0
HETATM   78  H   UNK     0       0.670  -1.385  -5.579  0.00  0.00           H+0
HETATM   79  H   UNK     0       1.151  -3.685  -4.581  0.00  0.00           H+0
HETATM   80  H   UNK     0       0.002  -2.886  -3.508  0.00  0.00           H+0
HETATM   81  H   UNK     0       3.976  -1.564  -3.180  0.00  0.00           H+0
HETATM   82  H   UNK     0       5.071  -3.534  -3.815  0.00  0.00           H+0
HETATM   83  H   UNK     0       3.587  -4.294  -4.419  0.00  0.00           H+0
HETATM   84  H   UNK     0       5.245  -2.127  -5.766  0.00  0.00           H+0
HETATM   85  H   UNK     0       4.672  -3.659  -6.462  0.00  0.00           H+0
HETATM   86  H   UNK     0       3.241  -1.458  -6.960  0.00  0.00           H+0
HETATM   87  H   UNK     0       2.379  -2.919  -6.441  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    3   41    1                                                  
CONECT    3    4    2   47                                                  
CONECT    4    3   40    5                                                  
CONECT    5    6    4   37                                                  
CONECT    6   31    7    5   48                                             
CONECT    7    8    6   49   50                                             
CONECT    8    7    9   29                                                  
CONECT    9   10    8   26                                                  
CONECT   10    9   51   19   11                                             
CONECT   11   12   10   52   53                                             
CONECT   12   13   17   11                                                  
CONECT   13   12   14   54                                                  
CONECT   14   15   13   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   12   18   25                                             
CONECT   18   19   17   55   56                                             
CONECT   19   20   18   10   57                                             
CONECT   20   19   25   21                                                  
CONECT   21   20   22   58   59                                             
CONECT   22   23   21   60   61                                             
CONECT   23   24   22   62   63                                             
CONECT   24   25   23   64   65                                             
CONECT   25   66   17   20   24                                             
CONECT   26   27    9   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   30   36   28    8                                             
CONECT   30   31   29   67   68                                             
CONECT   31    6   32   30   69                                             
CONECT   32   33   36   31                                                  
CONECT   33   34   32   70   71                                             
CONECT   34   35   33   72   73                                             
CONECT   35   36   34   74   75                                             
CONECT   36   76   35   32   29                                             
CONECT   37   38    5   77                                                  
CONECT   38   46   39   37   78                                             
CONECT   39   38   40   79   80                                             
CONECT   40   39   42   41    4                                             
CONECT   41    2   40                                                       
CONECT   42   43   46   40   81                                             
CONECT   43   42   44   82   83                                             
CONECT   44   43   45   84   85                                             
CONECT   45   44   46   86   87                                             
CONECT   46   45   42   38                                                  
CONECT   47    3                                                            
CONECT   48    6                                                            
CONECT   49    7                                                            
CONECT   50    7                                                            
CONECT   51   10                                                            
CONECT   52   11                                                            
CONECT   53   11                                                            
CONECT   54   13                                                            
CONECT   55   18                                                            
CONECT   56   18                                                            
CONECT   57   19                                                            
CONECT   58   21                                                            
CONECT   59   21                                                            
CONECT   60   22                                                            
CONECT   61   22                                                            
CONECT   62   23                                                            
CONECT   63   23                                                            
CONECT   64   24                                                            
CONECT   65   24                                                            
CONECT   66   25                                                            
CONECT   67   30                                                            
CONECT   68   30                                                            
CONECT   69   31                                                            
CONECT   70   33                                                            
CONECT   71   33                                                            
CONECT   72   34                                                            
CONECT   73   34                                                            
CONECT   74   35                                                            
CONECT   75   35                                                            
CONECT   76   36                                                            
CONECT   77   37                                                            
CONECT   78   38                                                            
CONECT   79   39                                                            
CONECT   80   39                                                            
CONECT   81   42                                                            
CONECT   82   43                                                            
CONECT   83   43                                                            
CONECT   84   44                                                            
CONECT   85   44                                                            
CONECT   86   45                                                            
CONECT   87   45                                                            
MASTER        0    0    0    0    0    0    0    0   87    0  196    0
END

RDKit          3D

87 98  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₄₁N₃O₆

Average Mass

623.7500 Da

Monoisotopic Mass

623.29954 Da

IUPAC Name

(1R,2R,8R,9S)-9-[(1S,7S,8S,13R)-3-oxo-7-[(1S,8S,13R)-3-oxo-2-oxa-9-azatetracyclo[6.5.1.0^{1,5}.0^{9,13}]tetradeca-4,6-dien-6-yl]-2-oxa-9-azatetracyclo[6.5.1.0^{1,5}.0^{9,13}]tetradec-4-en-4-yl]-14-oxa-7-azatetracyclo[6.6.1.0^{1,11}.0^{2,7}]pentadec-11-en-13-one

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]C1=C2C(=C([H])[C@@]3([H])N4C([H])([H])C([H])([H])C([H])([H])[C@]4([H])[C@]2(OC1=O)C3([H])[H])[C@]1([H])C([H])([H])C2=C(C(=O)O[C@@]22C([H])([H])[C@]1([H])N1C([H])([H])C([H])([H])C([H])([H])[C@]21[H])[C@]1([H])C([H])([H])C2=C([H])C(=O)O[C@]22C([H])([H])[C@@]1([H])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]21[H]

InChI Identifier

InChI=1S/C37H41N3O6/c41-31-12-19-11-23(27-17-35(19,44-31)28-5-1-2-8-39(27)28)33-25-14-22(26-18-37(25,46-34(33)43)30-7-4-10-40(26)30)21-13-20-16-36(24(21)15-32(42)45-36)29-6-3-9-38(20)29/h12-13,15,20,22-23,26-30H,1-11,14,16-18H2/t20-,22+,23-,26+,27-,28-,29-,30-,35-,36+,37+/m1/s1

InChI Key

HYWYNBKAWUIHFN-NOLXPYPPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Flueggea virosa	JEOL database	Zhang, H., et al, Org. Lett.,15 120 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indolizidines

Sub Class

Not Available

Direct Parent

Indolizidines

Alternative Parents

Substituents

Indolizidine
Tricarboxylic acid or derivatives
Pyrrolizidine
Azepane
Azepine
2-furanone
Piperidine
N-alkylpyrrolidine
Dihydrofuran
Pyrrolidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Lactone
Carboxylic acid ester
Azacycle
Oxacycle
Carboxylic acid derivative
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.67	ALOGPS
logP	2.4	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	10.15	ChemAxon
Physiological Charge	3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.62 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	168.4 m³·mol⁻¹	ChemAxon
Polarizability	67.84 Å³	ChemAxon
Number of Rings	12	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

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

71544999

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:29437326 ]
Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
Authors unspecified: Stomach (Gastric) Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389468 ]
Authors unspecified: Childhood Central Nervous System Atypical Teratoid/Rhabdoid Tumor Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389426 ]
Zhang, H., et al. (2013). Zhang, H., et al, Org. Lett.,15 120 (2013). Org. Lett..

Showing NP-Card for fluevirosine B (NP0043148)

MOL for NP0043148 (fluevirosine B)

3D MOL for NP0043148 (fluevirosine B)

3D SDF for NP0043148 (fluevirosine B)

3D-SDF for NP0043148 (fluevirosine B)

PDB for NP0043148 (fluevirosine B)

3D PDB for NP0043148 (fluevirosine B)

SMILES for NP0043148 (fluevirosine B)

INCHI for NP0043148 (fluevirosine B)

Structure for NP0043148 (fluevirosine B)

3D Structure for NP0043148 (fluevirosine B)