NP-MRD: Showing NP-Card for 18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid (NP0256151)

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Record Information

Version

2.0

Created at

2022-09-07 20:52:47 UTC

Updated at

2022-09-07 20:52:48 UTC

NP-MRD ID

NP0256151

Secondary Accession Numbers

None

Natural Product Identification

Common Name

18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid

Description

18-Hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Henicosa-2(10),4,6,8-tetraene-12-carboxylic acid belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor. 18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid is found in Adina eurhyncha. 18-Hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Henicosa-2(10),4,6,8-tetraene-12-carboxylic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251506202D          

 29 33  0  0  0  0            999 V2000
    3.1037   -1.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8316   -1.8790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700   -2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1805   -2.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0978   -3.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -3.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -2.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0151   -4.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -4.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9025   -5.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7131   -5.1582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2515   -5.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -5.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3342   -4.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7957   -4.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2239   -3.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0269   -3.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7048   -3.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4509   -3.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5191   -4.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8411   -4.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950   -4.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9852   -4.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6362   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793   -6.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5177   -7.1872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1688   -6.7158    0.0000 O   0  0  0  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  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 15 23  1  0  0  0  0
 18 23  1  0  0  0  0
 16 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 10 26  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
   -4.0641    3.8014    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3563    2.6068   -0.2063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7823    1.3746    0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7937    1.3963    1.0380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0990    0.1214   -0.0276 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7974   -1.0203    0.6596 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0868   -1.0979    0.1084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0489   -2.2759    0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7376   -2.2494    1.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1594   -0.9000    1.1943 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3503   -1.0207    1.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6278   -1.5455   -0.1935 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4823   -0.4135   -1.0785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8467    0.2333   -1.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6137    0.1468    0.2297 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5607    0.5527   -0.6915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6182    1.8405   -0.3409 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8968    2.1803   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5071    3.3549    0.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8730    3.4194    0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6207    2.2670    0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0414    1.0707   -0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6730    1.0466   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394    0.0332   -0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9506   -1.4009   -1.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051   -2.1524   -0.2824 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8422   -3.5252   -0.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8813   -4.2088   -1.0543 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -4.0890   -1.3317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1531    3.5115    0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8381    4.1009    1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8917    4.6036   -0.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2432   -0.0527   -1.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8911   -0.9135    1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3252   -2.0216   -0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8940   -2.2876   -0.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6597   -3.1470    0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9433   -2.7474    2.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0570   -2.9524    0.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3950   -0.5760    2.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7343   -1.7104    1.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8315   -0.0150    1.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7564   -0.7687   -2.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4780   -0.2255   -1.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105    1.2973   -1.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4400    1.1284    0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7994    2.4681   -0.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500    4.2650    0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3699    4.3471    0.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6922    2.3389    0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6287    0.1661   -0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9383   -1.8112   -0.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8204   -1.5350   -2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3112   -2.3315    0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497   -4.6777   -0.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 26  1  0
 26 25  1  0
 25 24  1  0
 24 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16 13  1  0
 13 14  1  0
 14 15  1  0
 26 27  1  0
 27 29  1  0
 27 28  2  0
 15  5  1  0
 15 10  1  0
 13 12  1  0
 23 24  1  0
 23 18  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  6
  6 34  1  1
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  1
 11 41  1  0
 11 42  1  0
 26 54  1  1
 25 52  1  0
 25 53  1  0
 17 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 22 51  1  0
 13 43  1  6
 14 44  1  0
 14 45  1  0
 15 46  1  1
 29 55  1  0
M  END


  Mrv1533004251506202D          

 29 33  0  0  0  0            999 V2000
    3.1037   -1.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8316   -1.8790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700   -2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1805   -2.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0978   -3.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -3.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -2.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0151   -4.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -4.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9025   -5.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7131   -5.1582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2515   -5.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -5.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3342   -4.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7957   -4.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2239   -3.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0269   -3.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7048   -3.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4509   -3.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5191   -4.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8411   -4.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950   -4.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9852   -4.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6362   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793   -6.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5177   -7.1872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1688   -6.7158    0.0000 O   0  0  0  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  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 15 23  1  0  0  0  0
 18 23  1  0  0  0  0
 16 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 10 26  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256151

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1C(O)CCC2CN3C(CC4=C(NC5=CC=CC=C45)C3CC12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O5/c1-29-22(28)19-13-8-16-20-14(12-4-2-3-5-15(12)23-20)9-17(21(26)27)24(16)10-11(13)6-7-18(19)25/h2-5,11,13,16-19,23,25H,6-10H2,1H3,(H,26,27)

> <INCHI_KEY>
FKDCWOOHMIPXRV-UHFFFAOYSA-N

> <FORMULA>
C22H26N2O5

> <MOLECULAR_WEIGHT>
398.459

> <EXACT_MASS>
398.184171945

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.981911887172096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
-0.8978080777237923

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.591693338426545

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4656237819749425

> <JCHEM_PKA_STRONGEST_BASIC>
7.749111193314168

> <JCHEM_POLAR_SURFACE_AREA>
102.86

> <JCHEM_REFRACTIVITY>
105.46089999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       5.794  -2.054   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.286  -3.507   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.291  -4.674   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.804  -4.387   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.783  -6.128   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.270  -6.415   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.265  -5.248   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.762  -7.869   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.767  -9.036   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.280  -8.749   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.285  -9.916   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       8.798  -9.629   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       9.803 -10.795   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.316 -10.508   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.824  -9.055   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.819  -7.888   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      11.618  -6.571   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      13.117  -6.925   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.382  -6.047   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.775  -6.704   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.902  -8.239   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.637  -9.117   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.244  -8.459   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.306  -8.175   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.301  -7.008   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.788  -7.295   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.295 -12.249   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.300 -13.416   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       7.782 -12.536   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14   27                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   15   18                                                  
CONECT   24   16   12   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25    5   10                                                  
CONECT   27   13   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
18-Hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0,.0,.0,]henicosa-2(10),4,6,8-tetraene-12-carboxylate	Generator
18-Hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylate	Generator

Chemical Formula

C₂₂H₂₆N₂O₅

Average Mass

398.4590 Da

Monoisotopic Mass

398.18417 Da

IUPAC Name

18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid

Traditional Name

18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C1C(O)CCC2CN3C(CC4=C(NC5=CC=CC=C45)C3CC12)C(O)=O

InChI Identifier

InChI=1S/C22H26N2O5/c1-29-22(28)19-13-8-16-20-14(12-4-2-3-5-15(12)23-20)9-17(21(26)27)24(16)10-11(13)6-7-18(19)25/h2-5,11,13,16-19,23,25H,6-10H2,1H3,(H,26,27)

InChI Key

FKDCWOOHMIPXRV-UHFFFAOYSA-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

Species Name	Source	Reference
Adina eurhyncha	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Yohimbine alkaloids

Sub Class

Not Available

Direct Parent

Yohimbine alkaloids

Alternative Parents

Substituents

Yohimbine
Corynanthean skeleton
Yohimbine alkaloid
Beta-carboline
Pyridoindole
Alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Beta-hydroxy acid
Aralkylamine
Dicarboxylic acid or derivatives
Hydroxy acid
Piperidine
Benzenoid
Pyrrole
Methyl ester
Heteroaromatic compound
Cyclic alcohol
Tertiary amine
Secondary alcohol
Tertiary aliphatic amine
Amino acid or derivatives
Carboxylic acid ester
Amino acid
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
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	1.65	ALOGPS
logP	-0.9	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	7.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	102.86 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.46 m³·mol⁻¹	ChemAxon
Polarizability	42.98 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid (NP0256151)

MOL for NP0256151 (18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid)

3D MOL for NP0256151 (18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid)

3D SDF for NP0256151 (18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid)

3D-SDF for NP0256151 (18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid)

PDB for NP0256151 (18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid)

3D PDB for NP0256151 (18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid)

SMILES for NP0256151 (18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid)

INCHI for NP0256151 (18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid)

Structure for NP0256151 (18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid)

3D Structure for NP0256151 (18-hydroxy-19-(methoxycarbonyl)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-12-carboxylic acid)