NP-MRD: Showing NP-Card for alpha-Yohimbine (NP0137547)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-30 16:55:49 UTC

Updated at

2022-05-30 16:55:50 UTC

NP-MRD ID

NP0137547

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Yohimbine

Description

Rauwolscine, also known as alpha-yohimbine or corynanthidine, belongs to the class of organic compounds known as chlorins. These are large heterocyclic aromatic ring systems consisting, at the core, of three pyrroles and one pyrroline coupled through four methine linkages. Rauwolscine is a very strong basic compound (based on its pKa). Rauwolscine acts predominantly as a α2-adrenergic receptor antagonist. It has also been shown to function as a 5-HT1A receptor partial agonist and 5-HT2A and 5-HT2B receptor antagonist. It is a stereoisomer of yohimbine. alpha-Yohimbine is found in Alstonia constricta, Corynanthe pachyceras, Rauvolfia caffra, Rauvolfia serpentina, Rauvolfia tetraphylla and Rauvolfia volkensii. Rauwolscine is a central nervous system stimulant, a local anesthetic and a vague aphrodisiac.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572004221604512D          

 31 35  0  0  1  0            999 V2000
    1.7070    2.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1223   -1.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0542   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4444   -1.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3081   -0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1568   -1.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6184   -0.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6653   -2.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8547   -2.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0500   -0.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5058   -2.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9673   -1.4501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6983   -1.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9374   -1.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2395   -0.6713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6301   -0.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885   -1.1426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8905   -0.1999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7011   -0.0462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3990   -0.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9732    0.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8271   -0.2837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3163   -1.9215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3521    0.4252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7838    0.8864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4348    1.3577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7779   -1.2964    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5116    0.1075    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1269   -1.7677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0800   -0.3536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1627    0.5789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13  4  2  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16  5  2  0  0  0  0
 16 13  1  0  0  0  0
 17 10  1  0  0  0  0
 18  7  1  0  0  0  0
 19 15  1  0  0  0  0
 19 18  1  0  0  0  0
 20 14  2  0  0  0  0
 20 17  1  0  0  0  0
 19 21  1  1  0  0  0
 22 16  1  0  0  0  0
 22 20  1  0  0  0  0
 23  9  1  0  0  0  0
 23 11  1  0  0  0  0
 23 17  1  0  0  0  0
 18 24  1  6  0  0  0
 25 21  2  0  0  0  0
 26  1  1  0  0  0  0
 26 21  1  0  0  0  0
 12 27  1  6  0  0  0
 15 28  1  6  0  0  0
 17 29  1  6  0  0  0
 18 30  1  1  0  0  0
 19 31  1  6  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -4.5992    2.4851    1.9763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2440    1.8993    0.7371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0527    1.1506    0.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3769    1.0570    1.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7908    0.5966   -0.7079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9600   -0.3403   -1.0428 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9818   -0.6946   -2.3687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0163   -1.5124   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6483   -1.9924    0.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6496   -1.6202   -0.7639 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3786   -2.3549   -0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7358   -1.6666   -0.1083 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9136   -2.4651   -0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780   -1.7892    0.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1726   -0.3301    0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0811    0.3437   -0.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3683    1.6463   -0.4072 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6268    1.8195    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3914    2.9722    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6908    2.9192    0.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2196    1.6874    0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    0.5327    0.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1660    0.5814    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8584   -0.3739   -0.7259 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3298    0.4280   -0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5272   -0.1259   -0.9127 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6392    2.1624    2.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5197    3.5790    1.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9568    2.0627    2.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9016    1.4423   -1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8771    0.2785   -0.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7107   -0.2001   -2.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6127   -1.2968    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5747   -2.3225   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3427   -1.6741    1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6822   -3.1059    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1591   -1.9943   -1.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546   -2.8072   -1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5620   -3.2608    0.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9855   -2.9551   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7731   -3.3218    0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5216   -2.0480    1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9889   -2.1825   -0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7455    2.4524   -0.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9702    3.9596   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2615    3.8316    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2512    1.6668    1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8910   -0.4329    0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908   -0.4242   -1.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3365    0.2091    0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2409    1.4923   -0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2294    0.0360   -1.9976 H   0  0  0  0  0  0  0  0  0  0  0  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 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
 16 24  1  0
 24 25  1  0
 25 26  1  0
 26  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
  5  6  1  0
 26 10  1  0
 24 12  1  0
 23 15  1  0
 23 18  1  0
  6 31  1  1
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  0
 11 39  1  0
 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
 24 49  1  6
 25 50  1  0
 25 51  1  0
 26 52  1  6
  5 30  1  6
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END


  Mrv1572004221604512D          

 31 35  0  0  1  0            999 V2000
    1.7070    2.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1223   -1.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0542   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4444   -1.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3081   -0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1568   -1.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6184   -0.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6653   -2.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8547   -2.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0500   -0.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5058   -2.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9673   -1.4501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6983   -1.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9374   -1.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2395   -0.6713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6301   -0.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885   -1.1426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8905   -0.1999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7011   -0.0462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3990   -0.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9732    0.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8271   -0.2837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3163   -1.9215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3521    0.4252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7838    0.8864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4348    1.3577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7779   -1.2964    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5116    0.1075    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1269   -1.7677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0800   -0.3536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1627    0.5789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13  4  2  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16  5  2  0  0  0  0
 16 13  1  0  0  0  0
 17 10  1  0  0  0  0
 18  7  1  0  0  0  0
 19 15  1  0  0  0  0
 19 18  1  0  0  0  0
 20 14  2  0  0  0  0
 20 17  1  0  0  0  0
 19 21  1  1  0  0  0
 22 16  1  0  0  0  0
 22 20  1  0  0  0  0
 23  9  1  0  0  0  0
 23 11  1  0  0  0  0
 23 17  1  0  0  0  0
 18 24  1  6  0  0  0
 25 21  2  0  0  0  0
 26  1  1  0  0  0  0
 26 21  1  0  0  0  0
 12 27  1  6  0  0  0
 15 28  1  6  0  0  0
 17 29  1  6  0  0  0
 18 30  1  1  0  0  0
 19 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0137547

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(O)CC[C@]2([H])CN3CCC4=C(NC5=CC=CC=C45)[C@]3([H])C[C@]2([H])[C@]1([H])C(=O)OC

> <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+/m1/s1

> <INCHI_KEY>
BLGXFZZNTVWLAY-DIRVCLHFSA-N

> <FORMULA>
C21H26N2O3

> <MOLECULAR_WEIGHT>
354.45

> <EXACT_MASS>
354.194342705

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.87472052270935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,15S,18S,19S,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>
16.38374584338826

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.676982087170042

> <JCHEM_PKA_STRONGEST_BASIC>
7.481317332411742

> <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>
rauwolscine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       3.186   3.988   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.295  -2.197   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.168  -0.662   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.030  -3.075   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.775  -0.005   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.159  -2.994   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.154  -1.827   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.708  -4.467   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.195  -4.754   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.693  -0.966   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.677  -3.874   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.672  -2.707   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.637  -2.418   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.216  -3.013   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.180  -1.253   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.510  -0.883   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.698  -2.133   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.662  -0.373   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.175  -0.086   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.211  -1.846   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.683   1.368   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       9.011  -0.530   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       6.190  -3.587   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       0.657   0.794   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.196   1.655   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.678   2.534   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       5.185  -2.420   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.688   0.201   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       7.703  -3.300   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.149  -0.660   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.170   1.081   0.000  0.00  0.00           H+0
CONECT    1   26                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   13                                                       
CONECT    5    3   16                                                       
CONECT    6    7   12                                                       
CONECT    7    6   18                                                       
CONECT    8    9   14                                                       
CONECT    9    8   23                                                       
CONECT   10   15   17                                                       
CONECT   11   12   23                                                       
CONECT   12    6   11   15   27                                             
CONECT   13    4   14   16                                                  
CONECT   14    8   13   20                                                  
CONECT   15   10   12   19   28                                             
CONECT   16    5   13   22                                                  
CONECT   17   10   20   23   29                                             
CONECT   18    7   19   24   30                                             
CONECT   19   15   18   21   31                                             
CONECT   20   14   17   22                                                  
CONECT   21   19   25   26                                                  
CONECT   22   16   20                                                       
CONECT   23    9   11   17                                                  
CONECT   24   18                                                            
CONECT   25   21                                                            
CONECT   26    1   21                                                       
CONECT   27   12                                                            
CONECT   28   15                                                            
CONECT   29   17                                                            
CONECT   30   18                                                            
CONECT   31   19                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
17alpha-Hydroxy-20alpha-yohimban-16beta-carboxylic acid methyl ester	ChEBI
alpha-Yohimbine	ChEBI
Corynanthidine	ChEBI
Isoyohimbine	ChEBI
Mesoyohimbine	ChEBI
Methyl (16beta,17alpha,20alpha)-17-hydroxyyohimban-16-carboxylate	ChEBI
17a-Hydroxy-20a-yohimban-16b-carboxylate methyl ester	Generator
17a-Hydroxy-20a-yohimban-16b-carboxylic acid methyl ester	Generator
17alpha-Hydroxy-20alpha-yohimban-16beta-carboxylate methyl ester	Generator
17Α-hydroxy-20α-yohimban-16β-carboxylate methyl ester	Generator
17Α-hydroxy-20α-yohimban-16β-carboxylic acid methyl ester	Generator
a-Yohimbine	Generator
Α-yohimbine	Generator
Methyl (16b,17a,20a)-17-hydroxyyohimban-16-carboxylate	Generator
Methyl (16b,17a,20a)-17-hydroxyyohimban-16-carboxylic acid	Generator
Methyl (16beta,17alpha,20alpha)-17-hydroxyyohimban-16-carboxylic acid	Generator
Methyl (16β,17α,20α)-17-hydroxyyohimban-16-carboxylate	Generator
Methyl (16β,17α,20α)-17-hydroxyyohimban-16-carboxylic acid	Generator
Methyl (1S,15S,18S,19S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid	Generator
Aphrodyne	MeSH
Hydrochloride, aphrodine	MeSH
Solvay brand OF yohimbine hydrochloride	MeSH
Yocon	MeSH
Yohimbine	MeSH
Aphrodine hydrochloride	MeSH
Palisades brand OF yohimbine hydrochloride	MeSH
Pluriviron	MeSH
Rauwolscine	MeSH
Corynanthine	MeSH
Kramer brand OF yohimbine hydrochloride	MeSH
Rauhimbine	MeSH
Yohimbine houdé	MeSH
Yohimex	MeSH
Hydrochloride, yohimbine	MeSH
Yohimbin spiegel	MeSH
Corynanthine tartrate	MeSH
Glenwood brand OF yohimbine hydrochloride	MeSH
Star brand OF yohimbine hydrochloride	MeSH
Tartrate, corynanthine	MeSH
StegroPharm brand OF yohimbine hydrochloride	MeSH
Aventis brand OF yohimbine hydrochloride	MeSH
Yohimbine hydrochloride	MeSH

Chemical Formula

C₂₁H₂₆N₂O₃

Average Mass

354.4500 Da

Monoisotopic Mass

354.19434 Da

IUPAC Name

methyl (1S,15S,18S,19S,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

rauwolscine

CAS Registry Number

Not Available

SMILES

[H][C@]1(O)CC[C@]2([H])CN3CCC4=C(NC5=CC=CC=C45)[C@]3([H])C[C@]2([H])[C@]1([H])C(=O)OC

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+/m1/s1

InChI Key

BLGXFZZNTVWLAY-DIRVCLHFSA-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
Alstonia constricta	LOTUS Database	35616633
Corynanthe pachyceras	LOTUS Database	35616633
Rauvolfia caffra	LOTUS Database	35616633
Rauvolfia serpentina	LOTUS Database	35616633
Rauvolfia tetraphylla	LOTUS Database	35616633
Rauvolfia volkensii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorins. These are large heterocyclic aromatic ring systems consisting, at the core, of three pyrroles and one pyrroline coupled through four methine linkages.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Chlorins

Direct Parent

Chlorins

Alternative Parents

Substituents

Chlorin
Tetracarboxylic acid or derivatives
Isoindole or derivatives
Fatty acid ester
Substituted pyrrole
Fatty acyl
Pyrrole
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methyl ester (CHEBI:60778 )
carboxylic acid (CHEBI:60778 )
beta-substituted porphyrin (CHEBI:60778 )

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)	7.48	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	39.87 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

Rauwolscine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

48562

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for alpha-Yohimbine (NP0137547)

MOL for NP0137547 (alpha-Yohimbine)

3D MOL for NP0137547 (alpha-Yohimbine)

3D SDF for NP0137547 (alpha-Yohimbine)

3D-SDF for NP0137547 (alpha-Yohimbine)

PDB for NP0137547 (alpha-Yohimbine)

3D PDB for NP0137547 (alpha-Yohimbine)

SMILES for NP0137547 (alpha-Yohimbine)

INCHI for NP0137547 (alpha-Yohimbine)

Structure for NP0137547 (alpha-Yohimbine)

3D Structure for NP0137547 (alpha-Yohimbine)