NP-MRD: Showing NP-Card for Pandicine (NP0068135)

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Record Information

Version

2.0

Created at

2022-04-28 13:08:22 UTC

Updated at

2022-04-28 13:08:22 UTC

NP-MRD ID

NP0068135

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pandicine

Description

Methyl (1S,12R,13R,15S,16R,20S)-16-[(E)-2-[(1R,12R,13S,18S)-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]Icosa-2(10),4,6,8,16-pentaen-17-yl]ethenyl]-12-ethyl-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2,4,6,9-tetraene-10-carboxylate belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. Pandicine is found in Pandacastrum saccharatum and Tabernaemontana ciliata. Based on a literature review very few articles have been published on methyl (1S,12R,13R,15S,16R,20S)-16-[(E)-2-[(1R,12R,13S,18S)-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]Icosa-2(10),4,6,8,16-pentaen-17-yl]ethenyl]-12-ethyl-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2,4,6,9-tetraene-10-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282215082D          

 55 65  0  0  1  0            999 V2000
    5.4910   -3.8122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0528   -4.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8105   -5.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064   -5.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4446   -4.7853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6869   -3.9967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6964   -5.1329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7958   -5.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1362   -6.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3773   -6.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2779   -5.3051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9374   -4.8095    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8381   -3.9905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791   -3.6671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4195   -4.1627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5189   -4.9816    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7599   -4.6582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6393   -2.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399   -1.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7809   -1.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6815   -0.3911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3411    0.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1000   -0.2190    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1994   -1.0380    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8488   -1.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1767   -0.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0773    0.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4279    0.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6089    0.4304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9036   -0.6408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0841   -0.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8255    0.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3873   -0.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9863   -0.9565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3339   -1.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1914   -0.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4337    0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8719    1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0678    1.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8146   -3.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2385   -4.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6183   -5.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8593   -5.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2356   -7.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5761   -7.7620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9946   -7.5899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0940   -8.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054   -6.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3723   -5.8092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1300   -6.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8569   -4.2319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0993   -3.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7333   -3.0236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  6  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  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
 15 17  1  1  0  0  0
 14 18  1  1  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 20  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  6  0  0  0
 27 32  1  6  0  0  0
 32 33  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 34 41  2  0  0  0  0
 13 42  1  0  0  0  0
 42 43  1  0  0  0  0
  7 43  1  0  0  0  0
 11 44  1  6  0  0  0
 44 45  1  0  0  0  0
  9 46  1  0  0  0  0
 46 47  2  0  0  0  0
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 48 49  1  0  0  0  0
  8 50  1  0  0  0  0
  4 50  1  0  0  0  0
  3 51  1  0  0  0  0
 51 52  1  0  0  0  0
  2 53  1  0  0  0  0
 53 54  1  0  0  0  0
  1 55  1  0  0  0  0
M  END

     RDKit          3D

105115  0  0  0  0  0  0  0  0999 V2000
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   -7.3174   -0.8800    3.2473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2610   -1.0621    4.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2464   -0.6249    1.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7935    1.0638   -0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4268    2.4633   -2.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8032    3.1938   -3.2369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7365    2.8470   -1.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3684    3.9080   -2.5601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1792    3.6276   -3.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3782    2.1240   -0.9508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6847    2.5065   -0.6244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8894    3.4970    0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580   -0.5368    0.2037 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.9014    1.2747   -1.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5895    0.3008   -0.0671 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.8765   -0.4449   -0.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1831   -0.0274   -0.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3936   -0.5500   -1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5987    0.0550   -0.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5660    1.1946    0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3550    1.7289    0.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1522    1.1096    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8533    1.3940    0.4621 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4709    2.5449    1.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3772   -1.6365   -1.4654 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8362    1.1604   -1.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6135    3.3122   -4.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9195    2.8263   -3.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7137    4.5864   -3.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7660    4.1350    0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1004    2.9871    1.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9793    4.1153    0.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6178   -1.4457   -1.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0978   -1.5837   -1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3468   -1.4993   -3.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1915    0.4236    0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4020   -1.4590   -1.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5132   -0.3896   -1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4834    1.6835    0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3707    2.6236    1.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3792    3.0772    1.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
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 53104  1  1
 55105  1  1
M  END


  Mrv1652304282215082D          

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  7 12  1  0  0  0  0
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 31 32  1  6  0  0  0
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 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  2  0  0  0  0
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 39 40  2  0  0  0  0
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 42 43  1  0  0  0  0
  7 43  1  0  0  0  0
 11 44  1  6  0  0  0
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  9 46  1  0  0  0  0
 46 47  2  0  0  0  0
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  8 50  1  0  0  0  0
  4 50  1  0  0  0  0
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 51 52  1  0  0  0  0
  2 53  1  0  0  0  0
 53 54  1  0  0  0  0
  1 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068135

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12CC(C(=O)OC)=C3NC4=C(OC)C(OC)=C(O)C=C4[C@]33CCN([C@H]13)[C@H](\C=C\C1=COC[C@@H]3[C@H]4CC5=C([C@@H](C[C@H]13)N4C)N(C)C1=CC=CC=C51)[C@@H]1O[C@H]21

> <INCHI_IDENTIFIER>
InChI=1S/C44H50N4O7/c1-7-43-19-26(41(50)53-6)39-44(28-18-33(49)37(51-4)38(52-5)34(28)45-39)14-15-48(42(43)44)30(36-40(43)55-36)13-12-22-20-54-21-27-24(22)16-32-35-25(17-31(27)46(32)2)23-10-8-9-11-29(23)47(35)3/h8-13,18,20,24,27,30-32,36,40,42,45,49H,7,14-17,19,21H2,1-6H3/b13-12+/t24-,27+,30-,31-,32-,36+,40+,42-,43+,44-/m1/s1

> <INCHI_KEY>
RKBLGNPKDGETAR-CVYLFQEVSA-N

> <FORMULA>
C44H50N4O7

> <MOLECULAR_WEIGHT>
746.905

> <EXACT_MASS>
746.367949966

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
105

> <JCHEM_AVERAGE_POLARIZABILITY>
79.66521095749718

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,12R,13R,15S,16R,20S)-16-[(E)-2-[(1R,12R,13S,18S)-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.0^{2,10}.0^{4,9}.0^{13,18}]icosa-2(10),4,6,8,16-pentaen-17-yl]ethenyl]-12-ethyl-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0^{1,9}.0^{2,7}.0^{13,15}.0^{17,20}]icosa-2,4,6,9-tetraene-10-carboxylate

> <ALOGPS_LOGP>
4.95

> <JCHEM_LOGP>
4.016190807000001

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.97036764537932

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.883886941616705

> <JCHEM_PKA_STRONGEST_BASIC>
7.685233964784903

> <JCHEM_POLAR_SURFACE_AREA>
110.19000000000001

> <JCHEM_REFRACTIVITY>
211.25179999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,12R,13R,15S,16R,20S)-16-[(E)-2-[(1R,12R,13S,18S)-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.0^{2,10}.0^{4,9}.0^{13,18}]icosa-2(10),4,6,8,16-pentaen-17-yl]ethenyl]-12-ethyl-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0^{1,9}.0^{2,7}.0^{13,15}.0^{17,20}]icosa-2,4,6,9-tetraene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      10.250  -7.116   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.299  -8.244   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.846  -9.716   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.345 -10.060   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.297  -8.933   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.749  -7.460   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.900  -9.581   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.085 -11.110   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.854 -12.035   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.438 -11.432   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.252  -9.903   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.483  -8.978   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       5.298  -7.449   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       3.881  -6.845   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.650  -7.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.835  -9.299   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.419  -8.695   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.695  -5.316   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.927  -4.391   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.741  -2.863   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.324  -2.259   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.139  -0.730   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.370   0.195   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.787  -0.409   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.972  -1.938   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.184  -2.887   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.713  -2.702   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.663  -1.490   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.478   0.039   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.265   0.989   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.737   0.803   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       7.287  -1.196   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       5.757  -1.020   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.874   0.688   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.923  -0.440   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      11.174  -1.786   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      11.823  -3.182   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.424  -0.095   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      13.876   1.377   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.828   2.504   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.327   2.160   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.121  -7.099   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       7.912  -8.421   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       3.021 -10.828   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       1.604 -10.224   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       6.040 -13.564   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       4.809 -14.489   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       7.457 -14.168   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       7.642 -15.697   0.000  0.00  0.00           C+0
HETATM   50  N   UNK     0       8.597 -11.406   0.000  0.00  0.00           N+0
HETATM   51  O   UNK     0      11.895 -10.844   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      11.443 -12.316   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      12.800  -7.900   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      13.252  -6.428   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      10.702  -5.644   0.000  0.00  0.00           O+0
CONECT    1    2    6   55                                                  
CONECT    2    1    3   53                                                  
CONECT    3    2    4   51                                                  
CONECT    4    3    5   50                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12   43                                             
CONECT    8    7    9   50                                                  
CONECT    9    8   10   46                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16   44                                             
CONECT   12   11    7   13                                                  
CONECT   13   12   14   42                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   11   17                                                  
CONECT   17   16   15                                                       
CONECT   18   14   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   20   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29   36                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   24   32                                                  
CONECT   32   31   27   33                                                  
CONECT   33   32                                                            
CONECT   34   29   35   41                                                  
CONECT   35   34   36   38                                                  
CONECT   36   35   28   37                                                  
CONECT   37   36                                                            
CONECT   38   35   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   34                                                       
CONECT   42   13   43                                                       
CONECT   43   42    7                                                       
CONECT   44   11   45                                                       
CONECT   45   44                                                            
CONECT   46    9   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48                                                            
CONECT   50    8    4                                                       
CONECT   51    3   52                                                       
CONECT   52   51                                                            
CONECT   53    2   54                                                       
CONECT   54   53                                                            
CONECT   55    1                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  130    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,12R,13R,15S,16R,20S)-16-[(e)-2-[(1R,12R,13S,18S)-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.0,.0,.0,]icosa-2(10),4,6,8,16-pentaen-17-yl]ethenyl]-12-ethyl-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0,.0,.0,.0,]icosa-2,4,6,9-tetraene-10-carboxylic acid	Generator

Chemical Formula

C₄₄H₅₀N₄O₇

Average Mass

746.9050 Da

Monoisotopic Mass

746.36795 Da

IUPAC Name

methyl (1S,12R,13R,15S,16R,20S)-16-[(E)-2-[(1R,12R,13S,18S)-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.0^{2,10}.0^{4,9}.0^{13,18}]icosa-2(10),4,6,8,16-pentaen-17-yl]ethenyl]-12-ethyl-4-hydroxy-5,6-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0^{1,9}.0^{2,7}.0^{13,15}.0^{17,20}]icosa-2,4,6,9-tetraene-10-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@@]12CC(C(=O)OC)=C3NC4=C(OC)C(OC)=C(O)C=C4[C@]33CCN([C@H]13)[C@H](\C=C\C1=COC[C@@H]3[C@H]4CC5=C([C@@H](C[C@H]13)N4C)N(C)C1=CC=CC=C51)[C@@H]1O[C@H]21

InChI Identifier

InChI=1S/C44H50N4O7/c1-7-43-19-26(41(50)53-6)39-44(28-18-33(49)37(51-4)38(52-5)34(28)45-39)14-15-48(42(43)44)30(36-40(43)55-36)13-12-22-20-54-21-27-24(22)16-32-35-25(17-31(27)46(32)2)23-10-8-9-11-29(23)47(35)3/h8-13,18,20,24,27,30-32,36,40,42,45,49H,7,14-17,19,21H2,1-6H3/b13-12+/t24-,27+,30-,31-,32-,36+,40+,42-,43+,44-/m1/s1

InChI Key

RKBLGNPKDGETAR-CVYLFQEVSA-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
Pandacastrum saccharatum	Plant	KNApSAcK
Tabernaemontana ciliata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Aspidosperma alkaloid
Pyridoindole
Carbazole
Beta-carboline
N-alkylindole
3-alkylindole
Indolizidine
Dihydroindole
Indole or derivatives
Indole
Anisole
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Secondary aliphatic/aromatic amine
Epoxypiperidine
Alkyl aryl ether
Para-oxazepine
Benzenoid
N-alkylpyrrolidine
Substituted pyrrole
Piperidine
N-methylpyrrole
Heteroaromatic compound
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrolidine
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Ether
Oxirane
Enamine
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	4.95	ALOGPS
logP	4.02	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	10.88	ChemAxon
pKa (Strongest Basic)	7.69	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.19 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	211.25 m³·mol⁻¹	ChemAxon
Polarizability	79.67 Å³	ChemAxon
Number of Rings	11	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162978263

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Pandicine (NP0068135)

MOL for NP0068135 (Pandicine)

3D MOL for NP0068135 (Pandicine)

3D SDF for NP0068135 (Pandicine)

3D-SDF for NP0068135 (Pandicine)

PDB for NP0068135 (Pandicine)

3D PDB for NP0068135 (Pandicine)

SMILES for NP0068135 (Pandicine)

INCHI for NP0068135 (Pandicine)

Structure for NP0068135 (Pandicine)

3D Structure for NP0068135 (Pandicine)