NP-MRD: Showing NP-Card for (1r,4r,12r,16s)-9-[(9r,16r)-14,16-dihydroxy-6-methyl-2-oxo-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-10,12,14-trien-9-yl]-7-hydroxy-8-methoxy-5-propanoyl-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9,20-tetraen-18-one (NP0244334)

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Record Information

Version

2.0

Created at

2022-09-07 05:06:27 UTC

Updated at

2022-09-07 05:06:27 UTC

NP-MRD ID

NP0244334

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4r,12r,16s)-9-[(9r,16r)-14,16-dihydroxy-6-methyl-2-oxo-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-10,12,14-trien-9-yl]-7-hydroxy-8-methoxy-5-propanoyl-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9,20-tetraen-18-one

Description

Cimilophytine belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine. Based on a literature review very few articles have been published on Cimilophytine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072207062D          

 50 59  0  0  1  0            999 V2000
    4.8608   -3.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4906   -2.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9441   -1.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677   -1.9013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5739   -1.1160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9528   -0.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3729    0.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5911    0.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3893    1.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6075    2.0037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0207    1.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0163    2.4402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2207    2.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6031    3.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6276    4.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3222    4.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0550    4.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7496    4.5164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0933    3.2471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7314    2.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8472    3.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3987    2.8019    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2745    3.6175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7673    0.8301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5046    1.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8589    0.9365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4416   -0.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2230   -0.3816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3472   -1.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7520    0.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2366    1.5116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5761    0.9057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8672    0.1338    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
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 21 27  1  0  0  0  0
 10 27  1  0  0  0  0
 20 28  1  0  0  0  0
 15 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  6  0  0  0
  9 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
  6 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35  7  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
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 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
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 44 45  1  0  0  0  0
 45  5  1  6  0  0  0
 35 45  1  0  0  0  0
 42 46  1  6  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 38  1  1  0  0  0
 42 50  1  0  0  0  0
 35 50  1  0  0  0  0
M  END

     RDKit          3D

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 46 91  1  0
 46 92  1  0
 37 80  1  0
 37 81  1  0
 36 78  1  0
 36 79  1  0
 34 77  1  0
 32 74  1  0
 32 75  1  0
 32 76  1  0
  8 56  1  0
 11 57  1  0
 11 58  1  0
 12 59  1  0
 12 60  1  0
 14 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  6
 16 65  1  0
 16 66  1  0
 17 67  1  0
 17 68  1  0
 23 69  1  0
 24 70  1  0
 25 71  1  0
 26 72  1  0
 29 73  1  0
 39 82  1  0
 39 83  1  0
 40 84  1  0
 41 85  1  0
M  END


  Mrv1652309072207062D          

 50 59  0  0  1  0            999 V2000
    4.8608   -3.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4906   -2.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9441   -1.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677   -1.9013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5739   -1.1160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9528   -0.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3729    0.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5911    0.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3893    1.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6075    2.0037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0207    1.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0163    2.4402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2207    2.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6031    3.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6276    4.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3222    4.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0550    4.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7496    4.5164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0933    3.2471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7314    2.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5470    2.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8472    3.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0623    2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7621    1.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9465    1.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4311    1.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3987    2.8019    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2745    3.6175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9692    0.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7673    0.8301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5046    1.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7509   -0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3308   -0.7611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6356   -0.1665    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1586    0.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7134    1.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8589    0.9365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9745    1.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3303    0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4416   -0.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2230   -0.3816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3472   -1.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1156   -1.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7598   -0.9821    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5337    0.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    0.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2366    1.5116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5761    0.9057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8672    0.1338    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 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
 17 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  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
 10 27  1  0  0  0  0
 20 28  1  0  0  0  0
 15 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  6  0  0  0
  9 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
  6 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35  7  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45  5  1  6  0  0  0
 35 45  1  0  0  0  0
 42 46  1  6  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 38  1  1  0  0  0
 42 50  1  0  0  0  0
 35 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244334

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)N1[C@@H]2CC[C@]34CC(=O)O[C@@]33N(CC[C@@]23C2=C1C(O)=C(OC)C(=C2)[C@@]12CCN(C)C3CCC(=O)N(C5=C(O)C=CC=C15)[C@@]23O)CC=C4

> <INCHI_IDENTIFIER>
InChI=1S/C38H42N4O8/c1-4-27(44)41-25-11-13-34-12-6-16-40-18-15-36(25,38(34,40)50-29(46)20-34)22-19-23(33(49-3)32(47)31(22)41)35-14-17-39(2)26-9-10-28(45)42(37(26,35)48)30-21(35)7-5-8-24(30)43/h5-8,12,19,25-26,43,47-48H,4,9-11,13-18,20H2,1-3H3/t25-,26?,34-,35-,36-,37+,38+/m1/s1

> <INCHI_KEY>
SLZIAOCXRLDVLI-UEHGBRQASA-N

> <FORMULA>
C38H42N4O8

> <MOLECULAR_WEIGHT>
682.774

> <EXACT_MASS>
682.300264328

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
70.52152601627755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4R,12R,16S)-9-[(9R,16R)-14,16-dihydroxy-6-methyl-2-oxo-1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-10,12,14-trien-9-yl]-7-hydroxy-8-methoxy-5-propanoyl-17-oxa-5,15-diazahexacyclo[13.4.3.0^{1,16}.0^{4,12}.0^{6,11}.0^{12,16}]docosa-6(11),7,9,20-tetraen-18-one

> <JCHEM_LOGP>
2.2572800142804703

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.164459988313498

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.431931643341702

> <JCHEM_PKA_STRONGEST_BASIC>
7.470401354084734

> <JCHEM_POLAR_SURFACE_AREA>
143.32

> <JCHEM_REFRACTIVITY>
192.2017

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,12R,16S)-9-[(9R,16R)-14,16-dihydroxy-6-methyl-2-oxo-1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-10,12,14-trien-9-yl]-7-hydroxy-8-methoxy-5-propanoyl-17-oxa-5,15-diazahexacyclo[13.4.3.0^{1,16}.0^{4,12}.0^{6,11}.0^{12,16}]docosa-6(11),7,9,20-tetraen-18-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       9.074  -6.122   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.383  -4.746   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.229  -3.459   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.766  -3.549   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.538  -2.083   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.245  -0.715   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.163   0.380   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.570   1.865   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.060   2.255   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.467   3.740   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.372   2.658   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.887   3.065   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       7.497   4.555   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       6.012   4.962   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.593   5.638   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.638   7.476   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.935   8.307   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.303   7.600   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.599   8.431   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      11.374   6.061   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      12.565   5.085   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.088   5.317   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.648   6.751   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      15.050   4.114   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.489   2.680   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.967   2.448   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.005   3.651   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.078   5.230   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.846   6.753   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.142   1.160   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.632   1.549   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.009   2.240   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.735  -0.325   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.818  -1.421   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.786  -0.311   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.763   0.880   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.932   2.177   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0       5.337   1.748   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0       3.686   2.333   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.483   1.370   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.691  -0.368   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.150  -0.712   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.381  -2.235   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.816  -2.795   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       7.018  -1.833   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       2.863   0.134   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       3.270   1.619   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       2.308   2.822   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       4.809   1.691   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       5.352   0.250   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   45                                                  
CONECT    6    5    7   33                                                  
CONECT    7    6    8   35                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   30                                                  
CONECT   10    9   11   27   28                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   28                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   21   10                                                  
CONECT   28   20   15   10   29                                             
CONECT   29   28                                                            
CONECT   30    9   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30    6   34                                                  
CONECT   34   33                                                            
CONECT   35    7   36   45   50                                             
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   50                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   46   50                                             
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44    5   35                                                  
CONECT   46   42   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50                                                       
CONECT   50   49   38   42   35                                             
MASTER        0    0    0    0    0    0    0    0   50    0  118    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₈H₄₂N₄O₈

Average Mass

682.7740 Da

Monoisotopic Mass

682.30026 Da

IUPAC Name

(1R,4R,12R,16S)-9-[(9R,16R)-14,16-dihydroxy-6-methyl-2-oxo-1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-10,12,14-trien-9-yl]-7-hydroxy-8-methoxy-5-propanoyl-17-oxa-5,15-diazahexacyclo[13.4.3.0^{1,16}.0^{4,12}.0^{6,11}.0^{12,16}]docosa-6(11),7,9,20-tetraen-18-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC(=O)N1[C@@H]2CC[C@]34CC(=O)O[C@@]33N(CC[C@@]23C2=C1C(O)=C(OC)C(=C2)[C@@]12CCN(C)C3CCC(=O)N(C5=C(O)C=CC=C15)[C@@]23O)CC=C4

InChI Identifier

InChI=1S/C38H42N4O8/c1-4-27(44)41-25-11-13-34-12-6-16-40-18-15-36(25,38(34,40)50-29(46)20-34)22-19-23(33(49-3)32(47)31(22)41)35-14-17-39(2)26-9-10-28(45)42(37(26,35)48)30-21(35)7-5-8-24(30)43/h5-8,12,19,25-26,43,47-48H,4,9-11,13-18,20H2,1-3H3/t25-,26?,34-,35-,36-,37+,38+/m1/s1

InChI Key

SLZIAOCXRLDVLI-UEHGBRQASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Indolonaphthyridine alkaloids

Sub Class

Not Available

Direct Parent

Indolonaphthyridine alkaloids

Alternative Parents

Substituents

Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Carbazole
Pyridoindole
Phenylpiperidine
Naphthyridine
Indole or derivatives
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Delta-lactam
Aralkylamine
Phenol
Piperidinone
Gamma butyrolactone
Benzenoid
N-alkylpyrrolidine
Piperidine
Pyrrolidine
Oxolane
Tertiary carboxylic acid amide
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Lactone
Lactam
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Ether
Alkanolamine
Azacycle
Carbonyl group
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.26	ChemAxon
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	7.47	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	143.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	192.2 m³·mol⁻¹	ChemAxon
Polarizability	70.52 Å³	ChemAxon
Number of Rings	10	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

102278015

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]