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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (12) Show 12 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:59 UTC

HMDB ID

HMDB0015464

Secondary Accession Numbers

HMDB15464

Metabolite Identification

Common Name

Yohimbine

Description

Yohimbine is only found in individuals that have used or taken this drug. It is a plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of impotence. It is also alleged to be an aphrodisiac. [PubChem]Yohimbine is a pre-synaptic alpha 2-adrenergic blocking agent. The exact mechanism for its use in impotence has not been fully elucidated. However, yohimbine may exert its beneficial effect on erectile ability through blockade of central alpha 2-adrenergic receptors producing an increase in sympathetic drive secondary to an increase in norepinephrine release and in firing rate of cells in the brain noradrenergic nuclei. Yohimbine-mediated norepinephrine release at the level of the corporeal tissues may also be involved. In addition, beneficial effects may involve other neurotransmitters such as dopamine and serotonin and cholinergic receptors.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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

HMDB0015464
     RDKit          3D
Yohimbine
 52 56  0  0  0  0  0  0  0  0999 V2000
   -5.1325    2.6398   -0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3599    1.4570   -0.1832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4388    1.3523    0.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3251    2.3532    1.6080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323    0.1344    1.0715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4779   -1.0831    1.3245 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7085   -0.6230    1.8286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7825   -1.8739    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5741   -2.2039   -0.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3746   -1.5376   -0.1491 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0891   -1.8466   -0.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199   -0.7752   -1.5240 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5950   -1.1934   -2.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799   -0.4621   -2.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0780    0.1609   -0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9841    0.6211   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4091    1.1477    0.9866 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7462    1.0334    1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398    1.4225    2.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9912    1.1955    1.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4442    0.5768    0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5472    0.1960   -0.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1748    0.4137   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6546    0.4456   -0.8287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3883    0.6577    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6859   -0.0482   -0.0893 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0984    2.5798    0.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2684    2.8363   -1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5852    3.5186    0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0072    0.2905    1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0553   -1.7445    2.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5619   -0.0297    2.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2284   -2.8409    0.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5915   -1.3723   -0.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4449   -3.2838   -0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7428   -1.7453   -1.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3018   -1.8825    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2623   -2.6824   -1.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6757   -2.2539   -0.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3045   -1.1657   -3.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7970   -2.2826   -2.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9600    0.3599   -2.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7444   -1.1264   -2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236    1.5724    1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2471    1.9122    2.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6842    1.5003    2.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5166    0.4116    0.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849   -0.2907   -1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5715    1.2937   -1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    1.7166    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0191    0.2290    1.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1402    0.3193   -1.0152 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 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
 26 10  1  0
 24 12  1  0
 23 15  1  0
 23 18  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  1
  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  1
 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
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>
HMDB0015464

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0015464
     RDKit          3D
Yohimbine
 52 56  0  0  0  0  0  0  0  0999 V2000
   -5.1325    2.6398   -0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3599    1.4570   -0.1832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4388    1.3523    0.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3251    2.3532    1.6080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323    0.1344    1.0715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4779   -1.0831    1.3245 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7085   -0.6230    1.8286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7825   -1.8739    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5741   -2.2039   -0.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3746   -1.5376   -0.1491 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0891   -1.8466   -0.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199   -0.7752   -1.5240 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5950   -1.1934   -2.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799   -0.4621   -2.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0780    0.1609   -0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9841    0.6211   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4091    1.1477    0.9866 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7462    1.0334    1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398    1.4225    2.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9912    1.1955    1.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4442    0.5768    0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5472    0.1960   -0.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1748    0.4137   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6546    0.4456   -0.8287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3883    0.6577    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6859   -0.0482   -0.0893 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0984    2.5798    0.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2684    2.8363   -1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5852    3.5186    0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0072    0.2905    1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0553   -1.7445    2.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5619   -0.0297    2.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2284   -2.8409    0.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5915   -1.3723   -0.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4449   -3.2838   -0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7428   -1.7453   -1.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3018   -1.8825    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2623   -2.6824   -1.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6757   -2.2539   -0.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3045   -1.1657   -3.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7970   -2.2826   -2.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9600    0.3599   -2.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7444   -1.1264   -2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236    1.5724    1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2471    1.9122    2.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6842    1.5003    2.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5166    0.4116    0.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849   -0.2907   -1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5715    1.2937   -1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    1.7166    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0191    0.2290    1.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1402    0.3193   -1.0152 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 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
 26 10  1  0
 24 12  1  0
 23 15  1  0
 23 18  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  1
  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  1
 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
M  END

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

COMPND    HMDB0015464
HETATM    1  C1  UNL     1      -5.133   2.640  -0.380  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.360   1.457  -0.183  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.439   1.352   0.856  1.00  0.00           C  
HETATM    4  O2  UNL     1      -3.325   2.353   1.608  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.632   0.134   1.072  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.478  -1.083   1.325  1.00  0.00           C  
HETATM    7  O3  UNL     1      -4.709  -0.623   1.829  1.00  0.00           O  
HETATM    8  C5  UNL     1      -3.783  -1.874   0.085  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.574  -2.204  -0.736  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.375  -1.538  -0.149  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.089  -1.847  -0.810  1.00  0.00           C  
HETATM   12  N1  UNL     1       0.520  -0.775  -1.524  1.00  0.00           N  
HETATM   13  C9  UNL     1       1.595  -1.193  -2.325  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.880  -0.462  -2.171  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.078   0.161  -0.864  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.984   0.621  -0.176  1.00  0.00           C  
HETATM   17  N2  UNL     1       2.409   1.148   0.987  1.00  0.00           N  
HETATM   18  C13 UNL     1       3.746   1.033   1.054  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.640   1.422   2.042  1.00  0.00           C  
HETATM   20  C15 UNL     1       5.991   1.195   1.884  1.00  0.00           C  
HETATM   21  C16 UNL     1       6.444   0.577   0.731  1.00  0.00           C  
HETATM   22  C17 UNL     1       5.547   0.196  -0.241  1.00  0.00           C  
HETATM   23  C18 UNL     1       4.175   0.414  -0.107  1.00  0.00           C  
HETATM   24  C19 UNL     1       0.655   0.446  -0.829  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.388   0.658   0.208  1.00  0.00           C  
HETATM   26  C21 UNL     1      -1.686  -0.048  -0.089  1.00  0.00           C  
HETATM   27  H1  UNL     1      -6.098   2.580   0.166  1.00  0.00           H  
HETATM   28  H2  UNL     1      -5.268   2.836  -1.465  1.00  0.00           H  
HETATM   29  H3  UNL     1      -4.585   3.519   0.026  1.00  0.00           H  
HETATM   30  H4  UNL     1      -2.007   0.291   1.975  1.00  0.00           H  
HETATM   31  H5  UNL     1      -3.055  -1.745   2.109  1.00  0.00           H  
HETATM   32  H6  UNL     1      -4.562  -0.030   2.606  1.00  0.00           H  
HETATM   33  H7  UNL     1      -4.228  -2.841   0.419  1.00  0.00           H  
HETATM   34  H8  UNL     1      -4.592  -1.372  -0.515  1.00  0.00           H  
HETATM   35  H9  UNL     1      -2.445  -3.284  -0.912  1.00  0.00           H  
HETATM   36  H10 UNL     1      -2.743  -1.745  -1.754  1.00  0.00           H  
HETATM   37  H11 UNL     1      -1.302  -1.882   0.923  1.00  0.00           H  
HETATM   38  H12 UNL     1      -0.262  -2.682  -1.543  1.00  0.00           H  
HETATM   39  H13 UNL     1       0.676  -2.254  -0.097  1.00  0.00           H  
HETATM   40  H14 UNL     1       1.304  -1.166  -3.401  1.00  0.00           H  
HETATM   41  H15 UNL     1       1.797  -2.283  -2.109  1.00  0.00           H  
HETATM   42  H16 UNL     1       2.960   0.360  -2.942  1.00  0.00           H  
HETATM   43  H17 UNL     1       3.744  -1.126  -2.379  1.00  0.00           H  
HETATM   44  H18 UNL     1       1.824   1.572   1.716  1.00  0.00           H  
HETATM   45  H19 UNL     1       4.247   1.912   2.947  1.00  0.00           H  
HETATM   46  H20 UNL     1       6.684   1.500   2.657  1.00  0.00           H  
HETATM   47  H21 UNL     1       7.517   0.412   0.636  1.00  0.00           H  
HETATM   48  H22 UNL     1       5.885  -0.291  -1.152  1.00  0.00           H  
HETATM   49  H23 UNL     1       0.572   1.294  -1.568  1.00  0.00           H  
HETATM   50  H24 UNL     1      -0.596   1.717   0.394  1.00  0.00           H  
HETATM   51  H25 UNL     1      -0.019   0.229   1.184  1.00  0.00           H  
HETATM   52  H26 UNL     1      -2.140   0.319  -1.015  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   26   30
CONECT    6    7    8   31
CONECT    7   32
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   26   37
CONECT   11   12   38   39
CONECT   12   13   24
CONECT   13   14   40   41
CONECT   14   15   42   43
CONECT   15   16   16   23
CONECT   16   17   24
CONECT   17   18   44
CONECT   18   19   19   23
CONECT   19   20   45
CONECT   20   21   21   46
CONECT   21   22   47
CONECT   22   23   23   48
CONECT   24   25   49
CONECT   25   26   50   51
CONECT   26   52
END

HMDB0015464
     RDKit          3D
Yohimbine
 52 56  0  0  0  0  0  0  0  0999 V2000
   -5.1325    2.6398   -0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3599    1.4570   -0.1832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4388    1.3523    0.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3251    2.3532    1.6080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323    0.1344    1.0715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4779   -1.0831    1.3245 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7085   -0.6230    1.8286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7825   -1.8739    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5741   -2.2039   -0.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3746   -1.5376   -0.1491 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0891   -1.8466   -0.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199   -0.7752   -1.5240 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5950   -1.1934   -2.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799   -0.4621   -2.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0780    0.1609   -0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9841    0.6211   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4091    1.1477    0.9866 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7462    1.0334    1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398    1.4225    2.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9912    1.1955    1.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4442    0.5768    0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5472    0.1960   -0.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1748    0.4137   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6546    0.4456   -0.8287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3883    0.6577    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6859   -0.0482   -0.0893 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0984    2.5798    0.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2684    2.8363   -1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5852    3.5186    0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0072    0.2905    1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0553   -1.7445    2.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5619   -0.0297    2.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2284   -2.8409    0.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5915   -1.3723   -0.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4449   -3.2838   -0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7428   -1.7453   -1.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3018   -1.8825    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2623   -2.6824   -1.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6757   -2.2539   -0.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3045   -1.1657   -3.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7970   -2.2826   -2.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9600    0.3599   -2.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7444   -1.1264   -2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236    1.5724    1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2471    1.9122    2.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6842    1.5003    2.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5166    0.4116    0.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849   -0.2907   -1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5715    1.2937   -1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    1.7166    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0191    0.2290    1.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1402    0.3193   -1.0152 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 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
 26 10  1  0
 24 12  1  0
 23 15  1  0
 23 18  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  1
  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  1
 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
M  END

View in JSmol View Stereo Labels

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 Molecular Weight

354.4427

Monoisotopic Molecular Weight

354.194342708

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

146-48-5

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

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015464)

Source

Exogenous

Exogenous (HMDB: HMDB0015464)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	241 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.35 g/L	Not Available
LogP	2.73	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	186.5	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	183.632	31661259
DarkChem	[M-H]-	176.979	31661259
DeepCCS	[M-2H]-	218.187	30932474
DeepCCS	[M+Na]+	192.735	30932474
AllCCS	[M+H]+	187.7	32859911
AllCCS	[M+H-H2O]+	184.8	32859911
AllCCS	[M+NH4]+	190.4	32859911
AllCCS	[M+Na]+	191.1	32859911
AllCCS	[M-H]-	193.0	32859911
AllCCS	[M+Na-2H]-	193.0	32859911
AllCCS	[M+HCOO]-	193.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.7 minutes	32390414
Predicted by Siyang on May 30, 2022	10.7344 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.64 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	53.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1832.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	198.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	166.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	141.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	404.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	400.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	479.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	770.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	406.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1312.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	248.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	277.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	358.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	209.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	87.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Yohimbine	[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	4107.2	Standard polar	33892256
Yohimbine	[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	2821.2	Standard non polar	33892256
Yohimbine	[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	3403.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Yohimbine,1TMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C)CC[C@H]2CN3CCC4=C([NH]C5=CC=CC=C45)[C@@H]3C[C@@H]21	3300.1	Semi standard non polar	33892256
Yohimbine,1TMS,isomer #2	COC(=O)[C@H]1[C@@H](O)CC[C@H]2CN3CCC4=C([C@@H]3C[C@@H]21)N([Si](C)(C)C)C1=CC=CC=C41	3221.8	Semi standard non polar	33892256
Yohimbine,2TMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C)CC[C@H]2CN3CCC4=C([C@@H]3C[C@@H]21)N([Si](C)(C)C)C1=CC=CC=C41	3188.4	Semi standard non polar	33892256
Yohimbine,2TMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C)CC[C@H]2CN3CCC4=C([C@@H]3C[C@@H]21)N([Si](C)(C)C)C1=CC=CC=C41	3093.1	Standard non polar	33892256
Yohimbine,2TMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C)CC[C@H]2CN3CCC4=C([C@@H]3C[C@@H]21)N([Si](C)(C)C)C1=CC=CC=C41	3943.2	Standard polar	33892256
Yohimbine,1TBDMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]2CN3CCC4=C([NH]C5=CC=CC=C45)[C@@H]3C[C@@H]21	3496.1	Semi standard non polar	33892256
Yohimbine,1TBDMS,isomer #2	COC(=O)[C@H]1[C@@H](O)CC[C@H]2CN3CCC4=C([C@@H]3C[C@@H]21)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C41	3398.3	Semi standard non polar	33892256
Yohimbine,2TBDMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]2CN3CCC4=C([C@@H]3C[C@@H]21)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C41	3515.2	Semi standard non polar	33892256
Yohimbine,2TBDMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]2CN3CCC4=C([C@@H]3C[C@@H]21)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C41	3575.6	Standard non polar	33892256
Yohimbine,2TBDMS,isomer #1	COC(=O)[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]2CN3CCC4=C([C@@H]3C[C@@H]21)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C41	4053.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Yohimbine GC-MS (Non-derivatized) - 70eV, Positive	splash10-008i-0396000000-43448cca1e1ad4343ac0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Yohimbine GC-MS (1 TMS) - 70eV, Positive	splash10-00xs-2139200000-8288a21cfcdae82fc694	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Yohimbine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimbine , positive-QTOF	splash10-0006-3921000000-e28dd8692e2b8dd63330	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yohimbine 10V, Positive-QTOF	splash10-0a4r-0019000000-98fd50566f845231fbed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yohimbine 20V, Positive-QTOF	splash10-0a4r-0129000000-49a3b77851cb2f327e51	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yohimbine 40V, Positive-QTOF	splash10-0ffx-0891000000-1297a98bf2d980f32361	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yohimbine 10V, Negative-QTOF	splash10-0udi-0009000000-6448f2e7be3b7fa35128	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yohimbine 20V, Negative-QTOF	splash10-0udi-0009000000-a436855e9ddc5d8e061e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yohimbine 40V, Negative-QTOF	splash10-07ef-3956000000-386e3fa9fb16f1a30cf6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yohimbine 10V, Positive-QTOF	splash10-0a4i-0009000000-b3d998cb3c47c9700660	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yohimbine 20V, Positive-QTOF	splash10-0a4i-0009000000-42b2cee0514145bdbc16	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yohimbine 40V, Positive-QTOF	splash10-002g-0695000000-7eacdb4b3fbff0521dcd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yohimbine 10V, Negative-QTOF	splash10-0udi-0009000000-1bc1d16b561be98b6dbc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yohimbine 20V, Negative-QTOF	splash10-004i-0095000000-d9723526ae361fda41c5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Yohimbine 40V, Negative-QTOF	splash10-0f96-0192000000-a13fb9eefdc725558673	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01392	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01392	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01392

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001789

Chemspider ID

8622

KEGG Compound ID

C09256

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Yohimbine

METLIN ID

Not Available

PubChem Compound

8969

PDB ID

Not Available

ChEBI ID

10093

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

References

Laurila JM, Xhaard H, Ruuskanen JO, Rantanen MJ, Karlsson HK, Johnson MS, Scheinin M: The second extracellular loop of alpha2A-adrenoceptors contributes to the binding of yohimbine analogues. Br J Pharmacol. 2007 Aug;151(8):1293-304. Epub 2007 Jun 11. [PubMed:17558432 ]
Zadori ZS, Shujaa N, Fulop K, Dunkel P, Gyires K: Pre- and postsynaptic mechanisms in the clonidine- and oxymetazoline-induced inhibition of gastric motility in the rat. Neurochem Int. 2007 Oct;51(5):297-305. Epub 2007 Jun 30. [PubMed:17664022 ]
Paul BZ, Jin J, Kunapuli SP: Molecular mechanism of thromboxane A(2)-induced platelet aggregation. Essential role for p2t(ac) and alpha(2a) receptors. J Biol Chem. 1999 Oct 8;274(41):29108-14. [PubMed:10506165 ]
Kalkman HO, Loetscher E: alpha2C-Adrenoceptor blockade by clozapine and other antipsychotic drugs. Eur J Pharmacol. 2003 Feb 21;462(1-3):33-40. [PubMed:12591093 ]
Ozdogan UK, Lahdesmaki J, Scheinin M: The analgesic efficacy of partial opioid agonists is increased in mice with targeted inactivation of the alpha2A-adrenoceptor gene. Eur J Pharmacol. 2006 Jan 4;529(1-3):105-13. Epub 2005 Dec 2. [PubMed:16325800 ]
Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634 ]

Enzyme Details

4. Alpha-2B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:: ADRA2B
Uniprot ID:: P18089
Molecular weight:: 49953.1

References

Freitag A, Wessler I, Racke K: Adrenoceptor- and cholinoceptor-mediated mechanisms in the regulation of 5-hydroxytryptamine release from isolated tracheae of newborn rabbits. Br J Pharmacol. 1996 Sep;119(1):91-8. [PubMed:8872361 ]
Cleary L, Vandeputte C, Docherty JR: Investigation of neurotransmission in vas deferens from alpha(2A/D)-adrenoceptor knockout mice. Br J Pharmacol. 2002 Jul;136(6):857-64. [PubMed:12110610 ]
Gyires K, Mullner K, Ronai AZ: Functional evidence that gastroprotection can be induced by activation of central alpha(2B)-adrenoceptor subtypes in the rat. Eur J Pharmacol. 2000 May 19;396(2-3):131-5. [PubMed:10822066 ]
Takada K, Clark DJ, Davies MF, Tonner PH, Krause TK, Bertaccini E, Maze M: Meperidine exerts agonist activity at the alpha(2B)-adrenoceptor subtype. Anesthesiology. 2002 Jun;96(6):1420-6. [PubMed:12170055 ]
Alonso E, Garrido E, Diez-Fernandez C, Perez-Garcia C, Herradon G, Ezquerra L, Deuel TF, Alguacil LF: Yohimbine prevents morphine-induced changes of glial fibrillary acidic protein in brainstem and alpha2-adrenoceptor gene expression in hippocampus. Neurosci Lett. 2007 Jan 29;412(2):163-7. Epub 2006 Nov 22. [PubMed:17123717 ]
Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634 ]

Enzyme Details

5. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634 ]

Enzyme Details

6. 5-hydroxytryptamine receptor 1B

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1B
Uniprot ID:: P28222
Molecular weight:: 43567.5

References

Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634 ]
Kaumann AJ: Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors. Naunyn Schmiedebergs Arch Pharmacol. 1983 Jun;323(2):149-54. [PubMed:6136920 ]

Enzyme Details

7. 5-hydroxytryptamine receptor 1A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1A
Uniprot ID:: P08908
Molecular weight:: 46106.3

References

Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634 ]
Kaumann AJ: Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors. Naunyn Schmiedebergs Arch Pharmacol. 1983 Jun;323(2):149-54. [PubMed:6136920 ]

Enzyme Details

8. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Baxter GS, Murphy OE, Blackburn TP: Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle. Br J Pharmacol. 1994 May;112(1):323-31. [PubMed:8032658 ]
Kaumann AJ: Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors. Naunyn Schmiedebergs Arch Pharmacol. 1983 Jun;323(2):149-54. [PubMed:6136920 ]

Enzyme Details

9. 5-hydroxytryptamine receptor 2C

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: HTR2C
Uniprot ID:: P28335
Molecular weight:: 51820.7

References

Baxter GS, Murphy OE, Blackburn TP: Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle. Br J Pharmacol. 1994 May;112(1):323-31. [PubMed:8032658 ]
Kaumann AJ: Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors. Naunyn Schmiedebergs Arch Pharmacol. 1983 Jun;323(2):149-54. [PubMed:6136920 ]

Enzyme Details

10. 5-hydroxytryptamine receptor 1D

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1D
Uniprot ID:: P28221
Molecular weight:: 41906.4

References

Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634 ]

Only showing the first 10 proteins. There are 12 proteins in total.

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Showing metabocard for Yohimbine (HMDB0015464)

MOL for HMDB0015464 (Yohimbine)

3D MOL for HMDB0015464 (Yohimbine)

3D SDF for HMDB0015464 (Yohimbine)

3D-SDF for HMDB0015464 (Yohimbine)

PDB for HMDB0015464 (Yohimbine)

3D PDB for HMDB0015464 (Yohimbine)

SMILES for HMDB0015464 (Yohimbine)

INCHI for HMDB0015464 (Yohimbine)

Structure for HMDB0015464 (Yohimbine)

3D Structure for HMDB0015464 (Yohimbine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

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Underivatized

Predicted Kovats Retention Indices

Underivatized

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GC-MS Spectra

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