NP-MRD: Showing NP-Card for 18-beta-hydroxy-3-epi-alpha-yohimbine (NP0137863)

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Record Information

Version

2.0

Created at

2022-05-31 16:36:50 UTC

Updated at

2022-05-31 16:36:51 UTC

NP-MRD ID

NP0137863

Secondary Accession Numbers

None

Natural Product Identification

Common Name

18-beta-hydroxy-3-epi-alpha-yohimbine

Description

18-Beta-hydroxy-3-epi-alpha-yohimbine belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor. 18-beta-hydroxy-3-epi-alpha-yohimbine is found in Rauvolfia serpentina. Based on a literature review very few articles have been published on 18-Beta-hydroxy-3-epi-alpha-yohimbine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218362D          

 33 37  0  0  1  0            999 V2000
    1.4767   -3.5903    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0151   -4.2154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2046   -4.3692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -4.6868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1746   -4.5331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9025   -5.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7131   -5.1582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2515   -5.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -5.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3342   -4.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7957   -4.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2239   -3.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0269   -3.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7048   -3.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4509   -3.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5191   -4.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8411   -4.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950   -4.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9852   -4.3793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2573   -3.6005    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6362   -3.9080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9084   -3.1292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0978   -3.2829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5594   -2.6578    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700   -2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1805   -2.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8316   -1.8790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037   -1.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -3.4366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8257   -4.0617    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -2.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 14 19  1  0  0  0  0
 12 20  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  1  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -2.7599    4.0535   -0.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5696    2.6996   -0.3273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1799    1.7179   -1.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8817    2.0862   -2.0669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0491    0.2728   -0.8211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6151   -0.2096   -0.8781 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6990    0.4701    0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3211   -0.3471    0.7424 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7224    0.1478    0.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2410    1.3854    0.5380 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5467    1.3940    0.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5248    2.3639    0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8262    2.0665   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1564    0.7573   -0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1824   -0.2135   -0.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8662    0.0838   -0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7337   -0.6795    0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5146   -2.1369   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3946   -2.4926    0.9156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2484   -1.7527    0.5444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2299   -2.1731   -0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6769   -1.7079   -0.7824 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3834   -2.2261    0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1954   -1.2480    1.1921 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5265   -0.8343    2.3726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7448   -0.0935    0.4527 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1176   -0.2488    0.2224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9628    4.1046   -1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5886    4.5235   -0.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8043    4.5932   -0.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5719   -0.2662   -1.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2800    0.0041   -1.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3372    1.0587    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1497    1.2991   -0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1927   -0.1856    1.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235    2.2756    0.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2809    3.3829    0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5922    2.8356   -0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1703    0.4993   -0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4242   -1.2321   -0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4136   -2.7318    0.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1959   -2.3586   -1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7675   -2.2422    1.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1748   -3.5743    0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1572   -3.2779   -0.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2813   -1.6765   -1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1375   -2.0663   -1.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6626   -2.7003    1.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0123   -3.1012    0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0720   -1.8362    1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0606   -0.0821    2.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6706    0.8118    1.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3992   -1.1924    0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 25  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9  8  1  0
  8  7  1  0
  7  6  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 27  1  0
 26 24  1  0
  6 22  1  0
  8 20  1  0
 16 17  1  0
 16 11  1  0
 24 50  1  1
 25 51  1  0
 23 48  1  0
 23 49  1  0
 22 47  1  6
 21 45  1  0
 21 46  1  0
 19 43  1  0
 19 44  1  0
 18 41  1  0
 18 42  1  0
 10 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
  8 35  1  1
  7 33  1  0
  7 34  1  0
  6 32  1  6
  5 31  1  6
  1 28  1  0
  1 29  1  0
  1 30  1  0
 26 52  1  1
 27 53  1  0
M  END


  Mrv1652305312218362D          

 33 37  0  0  1  0            999 V2000
    1.4767   -3.5903    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0151   -4.2154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2046   -4.3692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -4.6868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1746   -4.5331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9025   -5.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7131   -5.1582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2515   -5.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -5.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3342   -4.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7957   -4.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2239   -3.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0269   -3.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7048   -3.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4509   -3.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5191   -4.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8411   -4.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950   -4.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9852   -4.3793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2573   -3.6005    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6362   -3.9080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9084   -3.1292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0978   -3.2829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5594   -2.6578    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700   -2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1805   -2.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8316   -1.8790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037   -1.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -3.4366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8257   -4.0617    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -2.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 14 19  1  0  0  0  0
 12 20  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0137863

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O4/c1-27-21(26)18-14-9-16-19-13(12-4-2-3-5-15(12)22-19)6-7-23(16)10-11(14)8-17(24)20(18)25/h2-5,11,14,16-18,20,22,24-25H,6-10H2,1H3/t11-,14+,16-,17-,18+,20+/m1/s1

> <INCHI_KEY>
MMVZFQGCDSDHSV-DOGZXOHNSA-N

> <FORMULA>
C21H26N2O4

> <MOLECULAR_WEIGHT>
370.449

> <EXACT_MASS>
370.189257325

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
40.5490705591745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,15S,17R,18R,19S,20S)-17,18-dihydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate

> <JCHEM_LOGP>
1.0237546530000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.107678042823256

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.569847977111518

> <JCHEM_PKA_STRONGEST_BASIC>
6.8538249653734935

> <JCHEM_POLAR_SURFACE_AREA>
85.79

> <JCHEM_REFRACTIVITY>
100.99249999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,15S,17R,18R,19S,20S)-17,18-dihydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0       2.757  -6.702   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       3.762  -7.869   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.249  -8.156   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.767  -9.036   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.280  -8.749   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       7.793  -8.462   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       7.285  -9.916   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       8.798  -9.629   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.803 -10.795   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.316 -10.508   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.824  -9.055   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.819  -7.888   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      11.618  -6.571   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      13.117  -6.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.382  -6.047   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.775  -6.704   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.902  -8.239   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.637  -9.117   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.244  -8.459   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.306  -8.175   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       9.814  -6.721   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       8.301  -7.008   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.788  -7.295   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       7.296  -5.841   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       5.783  -6.128   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       4.778  -4.961   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       6.291  -4.674   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.804  -4.387   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.286  -3.507   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.794  -2.054   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.270  -6.415   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0       5.275  -7.582   0.000  0.00  0.00           H+0
HETATM   33  O   UNK     0       3.265  -5.248   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   31                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   23                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   11   14                                                  
CONECT   20   12    8   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22    5   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26   27   31                                             
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   25    2   32   33                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
18-b-Hydroxy-3-epi-a-yohimbine	Generator
18-Β-hydroxy-3-epi-α-yohimbine	Generator

Chemical Formula

C₂₁H₂₆N₂O₄

Average Mass

370.4490 Da

Monoisotopic Mass

370.18926 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

81703-06-2

SMILES

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

InChI Identifier

InChI=1S/C21H26N2O4/c1-27-21(26)18-14-9-16-19-13(12-4-2-3-5-15(12)22-19)6-7-23(16)10-11(14)8-17(24)20(18)25/h2-5,11,14,16-18,20,22,24-25H,6-10H2,1H3/t11-,14+,16-,17-,18+,20+/m1/s1

InChI Key

MMVZFQGCDSDHSV-DOGZXOHNSA-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
Rauvolfia serpentina	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
Beta-hydroxy acid
Aralkylamine
Hydroxy acid
Piperidine
Benzenoid
Pyrrole
Heteroaromatic compound
Methyl ester
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Amino acid or derivatives
Carboxylic acid ester
1,2-diol
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

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

57257022

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102004710

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 18-beta-hydroxy-3-epi-alpha-yohimbine (NP0137863)

MOL for NP0137863 (18-beta-hydroxy-3-epi-alpha-yohimbine)

3D MOL for NP0137863 (18-beta-hydroxy-3-epi-alpha-yohimbine)

3D SDF for NP0137863 (18-beta-hydroxy-3-epi-alpha-yohimbine)

3D-SDF for NP0137863 (18-beta-hydroxy-3-epi-alpha-yohimbine)

PDB for NP0137863 (18-beta-hydroxy-3-epi-alpha-yohimbine)

3D PDB for NP0137863 (18-beta-hydroxy-3-epi-alpha-yohimbine)

SMILES for NP0137863 (18-beta-hydroxy-3-epi-alpha-yohimbine)

INCHI for NP0137863 (18-beta-hydroxy-3-epi-alpha-yohimbine)

Structure for NP0137863 (18-beta-hydroxy-3-epi-alpha-yohimbine)

3D Structure for NP0137863 (18-beta-hydroxy-3-epi-alpha-yohimbine)