NP-MRD: Showing NP-Card for Yohimbine (NP0050925)

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Record Information

Version

2.0

Created at

2022-04-27 22:23:26 UTC

Updated at

2022-04-27 22:23:26 UTC

NP-MRD ID

NP0050925

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Yohimbine

Description

Yohimbine, also known as quebrachin or aphrodine, 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. Yohimbine is found in Alstonia angustifolia, Alstonia macrophylla, Amsonia elliptica, Aspidosperma excelsum, Aspidosperma polyneuron, Catharanthus lanceus, Catharanthus roseus, Coryanthe johimbe, Corynanthe johimbe, Corynanthe pachyceras, Haplophyton crooksii L.Benson, Homo sapiens, Pausinylstalia yohimbe, Pausinystalia macroceras, Pausinystalia paniculata, Pausinystalia yohimbe , Pausinystalia yomhinbe, Pseudocinchona pachyceras, Rauvolfia biauriculata, Rauvolfia caffra, Rauvolfia mannii, Rauvolfia nitida, Rauvolfia salicifolia, Rauvolfia serpentina , Rauvolfia tetraphylla, Rauvolfia volkensii, Rauvolfia vomitoria , Rauvolfia yunnanensis, Rauwolfia nitida, Rauwolfia verticillata, Rauwolfia vomitoria and Tabernaemontana corymbosa. Yohimbine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

1392
  Mrv0541 02231215282D          

 29 33  0  0  1  0            999 V2000
    7.4130   -1.6490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0230   -2.0506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0083   -1.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5496    1.6862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    0.7958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0711    0.1221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6265    0.7388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2606    0.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0164    1.0940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3255   -0.7041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3639    1.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4746    0.5721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1696   -0.8904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7481   -0.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2371    1.2597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3034    2.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9909    2.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5240    2.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7855   -1.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1989    2.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9547    1.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6558    2.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1507    1.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8477    2.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5935    1.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4832   -2.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6391   -0.3466    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0474    1.2174    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5863    0.6236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  6  0  0  0
  2 19  1  0  0  0  0
  2 26  1  0  0  0  0
  3 19  2  0  0  0  0
  4  9  1  0  0  0  0
  4 11  1  0  0  0  0
  4 16  1  0  0  0  0
  5 15  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 27  1  6  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  7 28  1  1  0  0  0
  8  9  1  0  0  0  0
  9 15  1  0  0  0  0
  9 29  1  6  0  0  0
 10 13  1  0  0  0  0
 10 19  1  6  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 25  2  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -4.6870    3.3817    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2686    2.1227    0.5926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2623    1.3776    0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810    1.7916   -0.9899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8766    0.0908    0.6315 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0689   -0.8108    0.6221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8633   -0.5694   -0.5057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7539   -2.2620    0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6022   -2.7053   -0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3834   -1.9006    0.2818 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2281   -2.3685   -0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8714   -1.4959   -0.6276 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0952   -2.0367   -1.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9570   -0.9789   -1.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0966    0.1091   -0.7176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471    0.5499   -0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3021    1.5312    0.7562 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6319    1.7508    0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5139    2.5977    1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8629    2.5761    1.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3708    1.6834    0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4967    0.8348   -0.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1330    0.8438   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6905   -0.1258   -0.5122 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4403    0.3196    0.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6704   -0.4570   -0.0437 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6304    3.2509   -0.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8371    4.0559    0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8776    3.7520   -0.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5852    0.3182    1.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7042   -0.5335    1.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9487   -1.3923   -1.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6523   -2.8344    0.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5517   -2.5808    1.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7747   -2.6077   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4022   -3.7803    0.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1787   -2.0257    1.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1130   -3.3509   -0.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5978   -2.6011   -1.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6850   -2.3904   -0.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9188   -2.8867   -1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4505   -0.5395   -2.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9431   -1.4114   -1.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6354    2.0512    1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1469    3.3031    2.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5769    3.2440    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4206    1.6238   -0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8939    0.1262   -1.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4515    0.3005   -1.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2484    0.0460    1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6452    1.3809    0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7846   -0.3680   -1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
  5 26  1  0
 26 25  1  0
 25 24  1  0
 24 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 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
 12 11  1  0
 26 10  1  0
 16 24  1  0
 23 18  1  0
 11 10  1  0
 23 15  1  0
 10 37  1  1
  9 35  1  0
  9 36  1  0
  8 33  1  0
  8 34  1  0
  6 31  1  1
  7 32  1  0
  5 30  1  1
  1 27  1  0
  1 28  1  0
  1 29  1  0
 26 52  1  6
 25 50  1  0
 25 51  1  0
 24 49  1  6
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
 11 38  1  0
 11 39  1  0
M  END

1392
  Mrv0541 02231215282D          

 29 33  0  0  1  0            999 V2000
    7.4130   -1.6490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0230   -2.0506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0083   -1.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5496    1.6862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    0.7958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0711    0.1221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6265    0.7388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2606    0.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0164    1.0940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3255   -0.7041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3639    1.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4746    0.5721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1696   -0.8904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7481   -0.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2371    1.2597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3034    2.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9909    2.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5240    2.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7855   -1.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1989    2.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9547    1.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6558    2.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1507    1.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8477    2.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5935    1.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4832   -2.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6391   -0.3466    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0474    1.2174    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5863    0.6236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  6  0  0  0
  2 19  1  0  0  0  0
  2 26  1  0  0  0  0
  3 19  2  0  0  0  0
  4  9  1  0  0  0  0
  4 11  1  0  0  0  0
  4 16  1  0  0  0  0
  5 15  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 27  1  6  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  7 28  1  1  0  0  0
  8  9  1  0  0  0  0
  9 15  1  0  0  0  0
  9 29  1  6  0  0  0
 10 13  1  0  0  0  0
 10 19  1  6  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050925

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H](O)[C@H](C(=O)OC)[C@@]1([H])C[C@]1([H])N(CCC3=C1NC1=CC=CC=C31)C2

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1

> <INCHI_KEY>
BLGXFZZNTVWLAY-SCYLSFHTSA-N

> <FORMULA>
C21H26N2O3

> <MOLECULAR_WEIGHT>
354.4427

> <EXACT_MASS>
354.194342708

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
40.22053888004653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.0986582599999997

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.383745843650257

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.67698210024458

> <JCHEM_PKA_STRONGEST_BASIC>
7.651837319075204

> <JCHEM_POLAR_SURFACE_AREA>
65.56

> <JCHEM_REFRACTIVITY>
99.631

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
yohimbine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1392                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      13.838  -3.078   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.243  -3.828   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.349  -2.082   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      10.359   3.148   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       6.711   1.486   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      11.333   0.228   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.369   1.379   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.820   0.562   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.364   2.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.808  -1.314   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.879   2.849   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.953   1.068   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.383  -1.662   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.463  -0.463   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.909   2.351   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.900   4.562   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.450   3.766   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.445   4.871   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.800  -2.408   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.971   3.762   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.515   2.356   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.958   4.921   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.015   2.011   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.449   4.612   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.974   3.146   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.235  -4.921   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      10.526  -0.647   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      13.155   2.272   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       8.561   1.164   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2   19   26                                                       
CONECT    3   19                                                            
CONECT    4    9   11   16                                                  
CONECT    5   15   21                                                       
CONECT    6    7    8   10   27                                             
CONECT    7    6   11   12   28                                             
CONECT    8    6    9                                                       
CONECT    9    4    8   15   29                                             
CONECT   10    6   13   19                                                  
CONECT   11    4    7                                                       
CONECT   12    7   14                                                       
CONECT   13    1   10   14                                                  
CONECT   14   12   13                                                       
CONECT   15    5    9   17                                                  
CONECT   16    4   18                                                       
CONECT   17   15   18   20                                                  
CONECT   18   16   17                                                       
CONECT   19    2    3   10                                                  
CONECT   20   17   21   22                                                  
CONECT   21    5   20   23                                                  
CONECT   22   20   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   25                                                       
CONECT   25   23   24                                                       
CONECT   26    2                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29    9                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
(+)-Yohimbine	ChEBI
(16alpha,17alpha)-17-Hydroxyyohimban-16-carboxylic acid methyl ester	ChEBI
17alpha-Hydroxyyohimban-16alpha-carboxylic acid methyl ester	ChEBI
Aphrodine	ChEBI
Corynine	ChEBI
Johimbin	ChEBI
Quebrachin	ChEBI
Quebrachine	ChEBI
Yohimbic acid methyl ester	ChEBI
Yohimbin	ChEBI
(16a,17a)-17-Hydroxyyohimban-16-carboxylate methyl ester	Generator
(16a,17a)-17-Hydroxyyohimban-16-carboxylic acid methyl ester	Generator
(16alpha,17alpha)-17-Hydroxyyohimban-16-carboxylate methyl ester	Generator
(16Α,17α)-17-hydroxyyohimban-16-carboxylate methyl ester	Generator
(16Α,17α)-17-hydroxyyohimban-16-carboxylic acid methyl ester	Generator
17a-Hydroxyyohimban-16a-carboxylate methyl ester	Generator
17a-Hydroxyyohimban-16a-carboxylic acid methyl ester	Generator
17alpha-Hydroxyyohimban-16alpha-carboxylate methyl ester	Generator
17Α-hydroxyyohimban-16α-carboxylate methyl ester	Generator
17Α-hydroxyyohimban-16α-carboxylic acid methyl ester	Generator
Yohimbate methyl ester	Generator
Aphrodyne	HMDB
Aventis brand OF yohimbine hydrochloride	HMDB
Solvay brand OF yohimbine hydrochloride	HMDB
Yohimbine hydrochloride	HMDB
Aphrodine hydrochloride	HMDB
Hydrochloride, yohimbine	HMDB
Pluriviron	HMDB
Rauwolscine	HMDB
Palisades brand OF yohimbine hydrochloride	HMDB
Star brand OF yohimbine hydrochloride	HMDB
StegroPharm brand OF yohimbine hydrochloride	HMDB
Tartrate, corynanthine	HMDB
Corynanthine	HMDB
Corynanthine tartrate	HMDB
Glenwood brand OF yohimbine hydrochloride	HMDB
Hydrochloride, aphrodine	HMDB
Kramer brand OF yohimbine hydrochloride	HMDB
Rauhimbine	HMDB
Yocon	HMDB
Yohimbin spiegel	HMDB
Yohimbine houdé	HMDB
Yohimex	HMDB

Chemical Formula

C₂₁H₂₆N₂O₃

Average Mass

354.4427 Da

Monoisotopic Mass

354.19434 Da

IUPAC Name

methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

Traditional Name

yohimbine

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H](O)[C@H](C(=O)OC)[C@@]1([H])C[C@]1([H])N(CCC3=C1NC1=CC=CC=C31)C2

InChI Identifier

InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1

InChI Key

BLGXFZZNTVWLAY-SCYLSFHTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alstonia angustifolia	LOTUS Database	35616633
Alstonia macrophylla	LOTUS Database	35616633
Amsonia elliptica	LOTUS Database	35616633
Aspidosperma excelsum	LOTUS Database	35616633
Aspidosperma polyneuron	LOTUS Database	35616633
Catharanthus lanceus	LOTUS Database	35616633
Catharanthus roseus	LOTUS Database	35616633
Coryanthe johimbe	-	KNApSAcK
Corynanthe johimbe	Plant	KNApSAcK
Corynanthe pachyceras	LOTUS Database	35616633
Haplophyton crooksii L.Benson	Plant	KNApSAcK
Homo sapiens	Animalia	KNApSAcK
Pausinylstalia yohimbe	-	KNApSAcK
Pausinystalia macroceras	Plant	KNApSAcK
Pausinystalia paniculata	Plant	KNApSAcK
Pausinystalia yohimbe	Plant	KNApSAcK
Pausinystalia yomhinbe	Plant	KNApSAcK
Pseudocinchona pachyceras	LOTUS Database	35616633
Rauvolfia biauriculata	LOTUS Database	35616633
Rauvolfia caffra	LOTUS Database	35616633
Rauvolfia mannii	LOTUS Database	35616633
Rauvolfia nitida	Plant	KNApSAcK
Rauvolfia salicifolia	LOTUS Database	35616633
Rauvolfia serpentina	Plant	KNApSAcK
Rauvolfia tetraphylla	LOTUS Database	35616633
Rauvolfia volkensii	LOTUS Database	35616633
Rauvolfia vomitoria	Plant	KNApSAcK
Rauvolfia yunnanensis	Plant	KNApSAcK
Rauwolfia nitida	Plant	KNApSAcK
Rauwolfia verticillata	Plant	KNApSAcK
Rauwolfia vomitoria	Plant	KNApSAcK
Tabernaemontana corymbosa	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
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Beta-hydroxy acid
Hydroxy acid
Benzenoid
Piperidine
Heteroaromatic compound
Methyl ester
Cyclic alcohol
Pyrrole
Amino acid or derivatives
Tertiary aliphatic amine
Carboxylic acid ester
Tertiary amine
Secondary alcohol
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxide
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Amine
Carbonyl group
Organic oxygen compound
Alcohol
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methyl 17-hydroxy-20xi-yohimban-16-carboxylate (CHEBI:10093 )
Indole alkaloids (C09256 )

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	2.36	ALOGPS
logP	2.1	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	7.65	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.63 m³·mol⁻¹	ChemAxon
Polarizability	40.22 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