NP-MRD: Showing NP-Card for (1s,12s,13r,14s,15e,17s)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate (NP0212684)

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Record Information

Version

2.0

Created at

2022-09-05 11:25:17 UTC

Updated at

2022-09-05 11:25:17 UTC

NP-MRD ID

NP0212684

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,12s,13r,14s,15e,17s)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate

Description

Methyl (1S,12S,13R,14S,17S)-15-ethylidene-13-(hydroxymethyl)-17-oxo-3,17λ⁵-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]Octadeca-2(10),4,6,8-tetraene-13-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. Based on a literature review very few articles have been published on methyl (1S,12S,13R,14S,17S)-15-ethylidene-13-(hydroxymethyl)-17-oxo-3,17λ⁵-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]Octadeca-2(10),4,6,8-tetraene-13-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052213252D          

 27 31  0  0  1  0            999 V2000
   -1.4389   -0.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850    0.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2627    0.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2871    0.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    0.6214    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
    1.2242    1.4340    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.8938    0.6568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1650    0.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3854   -0.2352    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8279   -0.9407    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1616   -1.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2496   -2.2474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3599   -1.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0799   -2.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1720   -1.4258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7040   -2.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501   -0.3360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2834   -0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0240   -0.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7490    0.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038    1.1276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834    0.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857    0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4533    0.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2186   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4163   -0.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487   -0.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  7 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 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
 19 27  1  0  0  0  0
 22 27  1  0  0  0  0
M  CHG  2   5   1   6  -1
M  END

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -3.9306   -2.4852   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3384   -1.9523    0.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775   -1.1833    0.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5937   -0.5901    1.7898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2591   -0.2685    1.3622 N   0  0  1  0  0  4  0  0  0  0  0  0
    0.5747    0.0167    2.3896 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.2608   -1.4739    0.6952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2835   -1.5239   -0.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6248   -0.8109   -0.7300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3237    0.6676   -0.6232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9536    1.2055   -1.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7627    2.5739   -1.9314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5800    1.3510   -0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6149    0.6996   -0.0274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6503    2.7307   -0.0868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8018    3.4320    0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2530    0.8533    0.4133 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1086    1.1322   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0947    0.0520    0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7427   -1.2187    0.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465   -1.9312    0.8050 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9498   -1.1851    0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3002   -1.4536    0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2271   -0.4777    0.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7400    0.7586   -0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3943    1.0451   -0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714    0.0620    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951   -3.2446   -1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9002   -2.9859   -0.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2339   -1.6688   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7482   -2.1732    1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1490    0.2264    2.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5062   -1.4302    2.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0222   -2.3439    1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3758   -2.5609   -1.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3751   -0.9825   -1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427   -1.0714   -1.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897    0.6410   -2.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8908    1.0696   -2.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5335    2.9237   -1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7019    2.7955    0.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6331    3.8485    1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9214    4.2802   -0.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5794    1.7363    1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5301    2.0878    0.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2033    1.2872   -1.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8603   -2.9496    1.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6835   -2.4235    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3056   -0.6763    0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4315    1.5543   -0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0259    2.0345   -0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 13  1  0
 13 14  2  0
 10 13  1  1
 10 11  1  0
 11 12  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7 20  1  0
 20 19  2  0
 19 18  1  0
 18 17  1  0
 17  5  1  0
  5  6  1  1
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
 19 27  1  0
 27 26  2  0
 26 25  1  0
 25 24  2  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 17 10  1  0
 22 27  1  0
  3  9  1  0
  5  7  1  0
 21 20  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
  9 37  1  6
  8 35  1  0
  8 36  1  0
  7 34  1  1
 18 45  1  0
 18 46  1  0
 17 44  1  1
  4 32  1  0
  4 33  1  0
  2 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 26 51  1  0
 25 50  1  0
 24 49  1  0
 23 48  1  0
 21 47  1  0
M  CHG  2   5   1   6  -1
M  END


  Mrv1652309052213252D          

 27 31  0  0  1  0            999 V2000
   -1.4389   -0.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850    0.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2627    0.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2871    0.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    0.6214    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
    1.2242    1.4340    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.8938    0.6568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1650    0.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3854   -0.2352    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8279   -0.9407    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1616   -1.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2496   -2.2474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3599   -1.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0799   -2.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1720   -1.4258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7040   -2.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501   -0.3360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2834   -0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0240   -0.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7490    0.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038    1.1276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834    0.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857    0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4533    0.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2186   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4163   -0.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487   -0.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  7 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 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
 19 27  1  0  0  0  0
 22 27  1  0  0  0  0
M  CHG  2   5   1   6  -1
M  END
> <DATABASE_ID>
NP0212684

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]1(CO)[C@H]2C[C@H]3C4=C(C[C@@H]1[N@@+]3([O-])C\C2=C\C)C1=CC=CC=C1N4

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O4/c1-3-12-10-23(26)17-9-15(12)21(11-24,20(25)27-2)18(23)8-14-13-6-4-5-7-16(13)22-19(14)17/h3-7,15,17-18,22,24H,8-11H2,1-2H3/b12-3-/t15-,17-,18-,21+,23+/m0/s1

> <INCHI_KEY>
ATIZKZWYIGEWST-INJLXLBXSA-N

> <FORMULA>
C21H24N2O4

> <MOLECULAR_WEIGHT>
368.433

> <EXACT_MASS>
368.173607261

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.434445897740744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,12S,13R,14S,15E,17S)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate

> <JCHEM_LOGP>
0.9140104223333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.677474400585687

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.160872319356873

> <JCHEM_PKA_STRONGEST_BASIC>
2.4952335428698844

> <JCHEM_POLAR_SURFACE_AREA>
85.38

> <JCHEM_REFRACTIVITY>
102.19490000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12S,13R,14S,15E,17S)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.686  -0.936   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.025   0.455   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.490   0.578   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.536   1.770   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.020   1.160   0.000  0.00  0.00           N+1
HETATM    6  O   UNK     0       2.285   2.677   0.000  0.00  0.00           O-1
HETATM    7  C   UNK     0       3.535   1.226   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.175   0.220   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.719  -0.439   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.545  -1.756   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.302  -2.664   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.466  -4.195   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.539  -2.933   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.016  -4.382   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.054  -2.662   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.047  -3.839   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.707  -0.627   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.262  -1.045   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.645  -0.284   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.131   1.168   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       6.354   2.105   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       7.622   1.232   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.120   1.591   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.180   0.473   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.741  -1.003   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.244  -1.362   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.184  -0.244   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   17                                             
CONECT    6    5                                                            
CONECT    7    5    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9   11   13   17                                             
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   10    5   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19    7   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   19   22                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,12S,13R,14S,17S)-15-ethylidene-13-(hydroxymethyl)-17-oxo-3,17-diazapentacyclo[12.3.1.0,.0,.0,]octadeca-2(10),4,6,8-tetraene-13-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₄N₂O₄

Average Mass

368.4330 Da

Monoisotopic Mass

368.17361 Da

IUPAC Name

(1S,12S,13R,14S,15E,17S)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate

Traditional Name

(1S,12S,13R,14S,15E,17S)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(CO)[C@H]2C[C@H]3C4=C(C[C@@H]1[N@@+]3([O-])C\C2=C\C)C1=CC=CC=C1N4

InChI Identifier

InChI=1S/C21H24N2O4/c1-3-12-10-23(26)17-9-15(12)21(11-24,20(25)27-2)18(23)8-14-13-6-4-5-7-16(13)22-19(14)17/h3-7,15,17-18,22,24H,8-11H2,1-2H3/b12-3-/t15-,17-,18-,21+,23+/m0/s1

InChI Key

ATIZKZWYIGEWST-INJLXLBXSA-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 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
Corynanthean skeleton
Vobasan skeleton
Pyridoindole
Beta-carboline
3-alkylindole
Piperidinecarboxylic acid
Indole or derivatives
Indole
Quinuclidine
Beta-hydroxy acid
Benzenoid
Piperidine
Hydroxy acid
Trialkyl amine oxide
Heteroaromatic compound
Methyl ester
Pyrrole
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Trisubstituted n-oxide
Monocarboxylic acid or derivatives
Carboxylic acid derivative
N-oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.91	ChemAxon
pKa (Strongest Acidic)	13.16	ChemAxon
pKa (Strongest Basic)	2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.19 m³·mol⁻¹	ChemAxon
Polarizability	39.43 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

163185031

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,12s,13r,14s,15e,17s)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate (NP0212684)

MOL for NP0212684 ((1s,12s,13r,14s,15e,17s)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate)

3D MOL for NP0212684 ((1s,12s,13r,14s,15e,17s)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate)

3D SDF for NP0212684 ((1s,12s,13r,14s,15e,17s)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate)

3D-SDF for NP0212684 ((1s,12s,13r,14s,15e,17s)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate)

PDB for NP0212684 ((1s,12s,13r,14s,15e,17s)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate)

3D PDB for NP0212684 ((1s,12s,13r,14s,15e,17s)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate)

SMILES for NP0212684 ((1s,12s,13r,14s,15e,17s)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate)

INCHI for NP0212684 ((1s,12s,13r,14s,15e,17s)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate)

Structure for NP0212684 ((1s,12s,13r,14s,15e,17s)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate)

3D Structure for NP0212684 ((1s,12s,13r,14s,15e,17s)-15-ethylidene-13-(hydroxymethyl)-13-(methoxycarbonyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-17-ium-17-olate)