NP-MRD: Showing NP-Card for (1s,13r,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate (NP0287460)

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Record Information

Version

2.0

Created at

2022-09-09 16:33:06 UTC

Updated at

2022-09-09 16:33:06 UTC

NP-MRD ID

NP0287460

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,13r,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate

Description

Methyl (1S,13R,15S,16S,20S)-16-methyl-13-oxo-17-oxa-3,13λ⁵-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Henicosa-2(10),4,6,8,18-pentaene-19-carboxylate 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. (1s,13r,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate is found in Uncaria elliptica. Based on a literature review very few articles have been published on methyl (1S,13R,15S,16S,20S)-16-methyl-13-oxo-17-oxa-3,13λ⁵-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Henicosa-2(10),4,6,8,18-pentaene-19-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092218332D          

 27 31  0  0  1  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
    2.0151   -4.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2814   -5.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -4.6868    0.0000 C   0  0  2  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  3  2  0  0  0  0  0  0  0  0  0
    4.4409   -5.9370    0.0000 O   0  5  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  2  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  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 16 24  1  0  0  0  0
 19 24  1  0  0  0  0
 25 17  1  1  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
  5 27  1  0  0  0  0
 10 27  1  0  0  0  0
M  CHG  2  12   1  13  -1
M  END

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -3.8537    3.6810    2.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9884    2.5717    1.1749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8651    2.0119    0.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7404    2.4678    0.8850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9541    0.8739   -0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1742    0.3850   -0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2048   -0.6848   -1.4754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2486   -1.7147   -1.2240 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4399   -2.8375   -2.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8489   -1.2057   -1.2064 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0862   -1.9534   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3615   -1.7744   -0.3159 N   0  0  2  0  0  4  0  0  0  0  0  0
    0.6829   -2.6368   -1.3139 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.0562   -2.1437    0.8511 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428   -1.0658    1.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4967   -0.2121    0.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8884    0.1111   -0.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036    0.8781   -1.2268 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8345    1.0632   -0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0117    1.7500   -0.7262 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0179    1.7541    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8763    1.0671    1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7097    0.3699    1.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7288    0.3882    0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5304   -0.4258   -0.7710 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5013    0.5396   -0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7996    0.2527   -0.9471 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7654    3.8616    2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4106    3.4037    2.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2286    4.6195    1.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0557    0.8461   -0.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4567   -2.1954   -0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -3.7438   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1707   -2.5534   -3.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5394   -3.0647   -2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2979   -1.4857   -2.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4004   -1.6377    0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2783   -3.0367   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3581   -2.6599    1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284   -2.9410    0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5009   -1.5583    2.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886   -0.4940    2.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688    1.3080   -2.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1498    2.2968   -1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9230    2.3043    0.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6787    1.0712    2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5492   -0.1870    2.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3893   -0.4153   -1.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6023    0.4440    0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1603    1.5479   -0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6720    0.7592   -1.9537 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 17 25  1  0
 25 26  1  0
 26 27  1  0
 27  5  1  0
 27 10  1  0
 25 12  1  0
 24 16  1  0
 24 19  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  0
  8 32  1  1
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  6
 11 37  1  0
 11 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 18 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 25 48  1  6
 26 49  1  0
 26 50  1  0
 27 51  1  6
M  CHG  2  12   1  13  -1
M  END


  Mrv1652309092218332D          

 27 31  0  0  1  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
    2.0151   -4.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2814   -5.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -4.6868    0.0000 C   0  0  2  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  3  2  0  0  0  0  0  0  0  0  0
    4.4409   -5.9370    0.0000 O   0  5  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  2  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  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 16 24  1  0  0  0  0
 19 24  1  0  0  0  0
 25 17  1  1  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
  5 27  1  0  0  0  0
 10 27  1  0  0  0  0
M  CHG  2  12   1  13  -1
M  END
> <DATABASE_ID>
NP0287460

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](C)[C@@H]2C[N@+]3([O-])CCC4=C(NC5=CC=CC=C45)[C@@H]3C[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O4/c1-12-16-10-23(25)8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-27-12)21(24)26-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16-,19-,23+/m0/s1

> <INCHI_KEY>
FEPWCBNZAPJQDK-KXHMRZCYSA-N

> <FORMULA>
C21H24N2O4

> <MOLECULAR_WEIGHT>
368.433

> <EXACT_MASS>
368.173607261

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.840108048250926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13R,15S,16S,20S)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate

> <JCHEM_LOGP>
1.4283512076666662

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.936370726910734

> <JCHEM_PKA_STRONGEST_BASIC>
3.192711612956914

> <JCHEM_POLAR_SURFACE_AREA>
74.38

> <JCHEM_REFRACTIVITY>
101.88130000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13R,15S,16S,20S)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         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       3.762  -7.869   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.767  -9.036   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.259 -10.489   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+1
HETATM   13  O   UNK     0       8.290 -11.082   0.000  0.00  0.00           O-1
HETATM   14  C   UNK     0       9.803 -10.795   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.316 -10.508   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.824  -9.055   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.819  -7.888   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      11.618  -6.571   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      13.117  -6.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.382  -6.047   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.775  -6.704   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.902  -8.239   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.637  -9.117   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.244  -8.459   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.306  -8.175   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.301  -7.008   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.788  -7.295   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14   25                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   16   19                                                  
CONECT   25   17   12   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26    5   10                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,13R,15S,16S,20S)-16-methyl-13-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0,.0,.0,]henicosa-2(10),4,6,8,18-pentaene-19-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₄N₂O₄

Average Mass

368.4330 Da

Monoisotopic Mass

368.17361 Da

IUPAC Name

(1S,13R,15S,16S,20S)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate

Traditional Name

(1S,13R,15S,16S,20S)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](C)[C@@H]2C[N@+]3([O-])CCC4=C(NC5=CC=CC=C45)[C@@H]3C[C@H]12

InChI Identifier

InChI=1S/C21H24N2O4/c1-12-16-10-23(25)8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-27-12)21(24)26-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16-,19-,23+/m0/s1

InChI Key

FEPWCBNZAPJQDK-KXHMRZCYSA-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
Uncaria elliptica	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

18-oxayohimban
Ajmalicine-skeleton
Corynanthean skeleton
Yohimbine alkaloid
Pyridoindole
Beta-carboline
3-alkylindole
Indole or derivatives
Indole
Benzenoid
Piperidine
Trialkyl amine oxide
Heteroaromatic compound
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrole
Carboxylic acid ester
Oxacycle
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
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	1.43	ChemAxon
pKa (Strongest Acidic)	13.94	ChemAxon
pKa (Strongest Basic)	3.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.88 m³·mol⁻¹	ChemAxon
Polarizability	38.84 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

163186436

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,13r,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate (NP0287460)

MOL for NP0287460 ((1s,13r,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate)

3D MOL for NP0287460 ((1s,13r,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate)

3D SDF for NP0287460 ((1s,13r,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate)

3D-SDF for NP0287460 ((1s,13r,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate)

PDB for NP0287460 ((1s,13r,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate)

3D PDB for NP0287460 ((1s,13r,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate)

SMILES for NP0287460 ((1s,13r,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate)

INCHI for NP0287460 ((1s,13r,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate)

Structure for NP0287460 ((1s,13r,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate)

3D Structure for NP0287460 ((1s,13r,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaen-13-ium-13-olate)