NP-MRD: Showing NP-Card for (1s,10r,12s,13e,18s)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0⁹,¹⁵]octadeca-2,4,6-trien-15-ium (NP0309169)

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Record Information

Version

1.0

Created at

2022-09-11 03:33:49 UTC

Updated at

2022-09-11 03:33:50 UTC

NP-MRD ID

NP0309169

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,10r,12s,13e,18s)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0⁹,¹⁵]octadeca-2,4,6-trien-15-ium

Description

Echitaminic acid, also known as echitaminate, belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. (1s,10r,12s,13e,18s)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0⁹,¹⁵]octadeca-2,4,6-trien-15-ium is found in Alstonia rostrata. It was first documented in 2004 (PMID: 15387668). Based on a literature review very few articles have been published on Echitaminic acid (PMID: 27002397).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112205332D          

 27 31  0  0  1  0            999 V2000
   -1.2963   -0.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7957    0.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1205    0.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6704    1.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5459    0.6280    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.6956    0.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7846    1.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5797    1.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4323    0.4771    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2766    0.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9368    0.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6954    0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938   -0.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1336   -0.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -0.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5864   -0.7898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9645   -0.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -0.9519    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6924   -1.8092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267   -0.1414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5442    0.1656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1214    1.0502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4283    1.9822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6902    1.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3129    1.9437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8207    1.6864    0.0000 O   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  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  9 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 21 20  1  1  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  CHG  1   5   1
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
   -4.0721    0.2512    1.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2671    1.2039    0.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9733    0.9917    0.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3643    2.0696   -0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0283    1.7697   -0.8740 N   0  0  2  0  0  4  0  0  0  0  0  0
    0.6907    3.0650   -0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1533    1.1682   -2.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8046   -0.1914   -1.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5061   -0.5209   -0.4654 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7192   -1.1387    0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138   -2.3922    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4052   -2.5990    0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3622   -1.6073    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000   -0.3488    0.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6982   -0.1347    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1104    1.0941   -0.3949 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6966    0.9442    0.0182 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5305    1.1191    1.4563 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7088    1.2059    2.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3697    0.0131    2.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -0.2369    0.9928 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8010   -1.0448   -0.1677 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8872   -0.9316   -1.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5623   -1.5917   -2.4183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9319   -2.4906    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1521   -2.9119    1.3458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7992   -3.4080   -0.8401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0905    0.6728    1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516    0.1391    2.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2250   -0.7224    0.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7641    2.0951    0.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0215    2.4006   -1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3394    2.9639    0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2722    3.1870    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0393    3.9093   -0.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2826    3.1772   -1.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166    1.1492   -2.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9120    1.7708   -2.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9306   -0.0675   -2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5544   -0.9583   -2.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3982   -3.1744    0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6651   -3.6115    1.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3430   -1.8650    1.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644    0.4164    0.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5500    1.8961   -0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297    2.0764    1.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0405    0.3445    2.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198   -0.8890    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8072    0.3313    2.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2440   -0.8600    1.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2492    0.0537   -1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8085   -1.4990   -0.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3409   -1.9378   -2.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754   -4.3457   -0.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  9  8  1  6
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 17 16  1  1
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  1
 25 27  1  0
 25 26  2  0
 21  3  1  0
 17  5  1  0
 17  9  1  0
 22  9  1  0
 15 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  4 32  1  0
  4 33  1  0
  6 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 16 45  1  0
 18 46  1  6
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  1
 23 51  1  0
 23 52  1  0
 24 53  1  0
 27 54  1  0
M  CHG  1   5   1
M  END


  Mrv1652309112205332D          

 27 31  0  0  1  0            999 V2000
   -1.2963   -0.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7957    0.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1205    0.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6704    1.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5459    0.6280    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.6956    0.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7846    1.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5797    1.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4323    0.4771    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2766    0.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9368    0.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6954    0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938   -0.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1336   -0.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -0.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5864   -0.7898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9645   -0.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -0.9519    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6924   -1.8092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267   -0.1414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5442    0.1656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1214    1.0502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4283    1.9822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6902    1.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3129    1.9437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8207    1.6864    0.0000 O   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  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  9 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 21 20  1  1  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  CHG  1   5   1
M  END
> <DATABASE_ID>
NP0309169

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\C[N+]2(C)CC[C@@]34C5=CC=CC=C5NC23[C@H](O)C[C@@H]1[C@]4(CO)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O4/c1-3-13-11-23(2)9-8-20-14-6-4-5-7-16(14)22-21(20,23)17(25)10-15(13)19(20,12-24)18(26)27/h3-7,15,17,22,24-25H,8-12H2,1-2H3/p+1/b13-3-/t15-,17+,19+,20-,21?,23?/m0/s1

> <INCHI_KEY>
AHPUGTDAOMLACC-XHFYEUJQSA-O

> <FORMULA>
C21H27N2O4

> <MOLECULAR_WEIGHT>
371.456

> <EXACT_MASS>
371.196533778

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.11324492181671

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,10R,12S,13E,18S)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0^{1,9}.0^{2,7}.0^{9,15}]octadeca-2,4,6-trien-15-ium

> <JCHEM_LOGP>
-3.249494693805079

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.011206709470287

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.138392717403529

> <JCHEM_PKA_STRONGEST_BASIC>
1.8938677288872985

> <JCHEM_POLAR_SURFACE_AREA>
89.79

> <JCHEM_REFRACTIVITY>
114.08849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10R,12S,13E,18S)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0^{1,9}.0^{2,7}.0^{9,15}]octadeca-2,4,6-trien-15-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.420  -0.589   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.485   0.689   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.225   0.799   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.251   1.977   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.886   1.172   0.000  0.00  0.00           N+1
HETATM    6  C   UNK     0       1.299   0.665   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.331   2.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.815   2.440   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.540   0.891   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.116   0.567   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.349   1.490   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.765   0.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.948  -0.644   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.716  -1.568   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.300  -0.962   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.828  -1.474   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.667  -0.346   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.873  -1.777   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.159  -3.377   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.308  -1.832   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.357  -0.264   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.882   0.309   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.093   1.960   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.666   3.700   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.155   2.090   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.317   3.628   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.532   3.148   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   17                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17   22                                             
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    9    5   18                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20    3   22                                                  
CONECT   22   21    9   23   25                                             
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
Echitaminate	Generator

Chemical Formula

C₂₁H₂₇N₂O₄

Average Mass

371.4560 Da

Monoisotopic Mass

371.19653 Da

IUPAC Name

(1S,10R,12S,13E,18S)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0^{1,9}.0^{2,7}.0^{9,15}]octadeca-2,4,6-trien-15-ium

Traditional Name

(1S,10R,12S,13E,18S)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0^{1,9}.0^{2,7}.0^{9,15}]octadeca-2,4,6-trien-15-ium

CAS Registry Number

Not Available

SMILES

C\C=C1\C[N+]2(C)CC[C@@]34C5=CC=CC=C5NC23[C@H](O)C[C@@H]1[C@]4(CO)C(O)=O

InChI Identifier

InChI=1S/C21H26N2O4/c1-3-13-11-23(2)9-8-20-14-6-4-5-7-16(14)22-21(20,23)17(25)10-15(13)19(20,12-24)18(26)27/h3-7,15,17,22,24-25H,8-12H2,1-2H3/p+1/b13-3-/t15-,17+,19+,20-,21?,23?/m0/s1

InChI Key

AHPUGTDAOMLACC-XHFYEUJQSA-O

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

Species Name	Source	Reference
Alstonia rostrata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Pyrroloindole
Dihydroindole
Indole
Secondary aliphatic/aromatic amine
Beta-hydroxy acid
Azepane
Benzenoid
N-alkylpyrrolidine
Hydroxy acid
Tetraalkylammonium salt
Pyrrolidine
Pyrrole
Cyclic alcohol
Amino acid
Secondary alcohol
Amino acid or derivatives
Azacycle
Secondary amine
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Organic cation
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	-3.2	ChemAxon
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	1.89	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	89.79 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	114.09 m³·mol⁻¹	ChemAxon
Polarizability	39.11 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00043478

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

101352948

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang ML, Chen J, Sun M, Zhang DB, Gao K: Antifungal Indole Alkaloids from Winchia calophylla. Planta Med. 2016 May;82(8):712-6. doi: 10.1055/s-0042-102459. Epub 2016 Mar 22. [PubMed:27002397 ]
Salim AA, Garson MJ, Craik DJ: New indole alkaloids from the bark of Alstonia scholaris. J Nat Prod. 2004 Sep;67(9):1591-4. doi: 10.1021/np0498612. [PubMed:15387668 ]
LOTUS database [Link]

Showing NP-Card for (1s,10r,12s,13e,18s)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0⁹,¹⁵]octadeca-2,4,6-trien-15-ium (NP0309169)

MOL for NP0309169 ((1s,10r,12s,13e,18s)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0⁹,¹⁵]octadeca-2,4,6-trien-15-ium)

3D MOL for NP0309169 ((1s,10r,12s,13e,18s)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0⁹,¹⁵]octadeca-2,4,6-trien-15-ium)

3D SDF for NP0309169 ((1s,10r,12s,13e,18s)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0⁹,¹⁵]octadeca-2,4,6-trien-15-ium)

3D-SDF for NP0309169 ((1s,10r,12s,13e,18s)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0⁹,¹⁵]octadeca-2,4,6-trien-15-ium)

PDB for NP0309169 ((1s,10r,12s,13e,18s)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0⁹,¹⁵]octadeca-2,4,6-trien-15-ium)

3D PDB for NP0309169 ((1s,10r,12s,13e,18s)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0⁹,¹⁵]octadeca-2,4,6-trien-15-ium)

SMILES for NP0309169 ((1s,10r,12s,13e,18s)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0⁹,¹⁵]octadeca-2,4,6-trien-15-ium)

INCHI for NP0309169 ((1s,10r,12s,13e,18s)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0⁹,¹⁵]octadeca-2,4,6-trien-15-ium)

Structure for NP0309169 ((1s,10r,12s,13e,18s)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0⁹,¹⁵]octadeca-2,4,6-trien-15-ium)

3D Structure for NP0309169 ((1s,10r,12s,13e,18s)-18-carboxy-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0⁹,¹⁵]octadeca-2,4,6-trien-15-ium)