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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:11:48 UTC

Update Date

2022-09-22 18:35:01 UTC

HMDB ID

HMDB0341123

Secondary Accession Numbers

None

Metabolite Identification

Common Name

7alpha-Voacangine hydroxyindolenine

Description

9H-Voacangine, 9-hydroxy- belongs to the class of organic compounds known as ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond. Based on a literature review very few articles have been published on 9H-Voacangine, 9-hydroxy-.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092221502D          

 31 35  0  0  1  0            999 V2000
   -0.1940    0.2161    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292    0.1605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9757    0.9154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898    0.9839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4141    1.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2317    1.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5990    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0504    1.3896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4103    0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5190   -0.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815   -0.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9355   -0.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8268    0.6681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5541    1.1449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3808    0.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0643    0.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7747   -0.6939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2062   -0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3131   -0.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491   -0.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4215   -1.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -1.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0828   -1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8865   -2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0966    0.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655    0.5006    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7519   -0.6464    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2595   -1.3084    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0645   -1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695   -2.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8681   -0.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  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  1  0  0  0  0
 13 16  2  0  0  0  0
  9 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  6  0  0  0
 29 30  1  0  0  0  0
 27 31  1  0  0  0  0
  2 31  1  0  0  0  0
M  END


  Mrv1652309092221502D          

 31 35  0  0  1  0            999 V2000
   -0.1940    0.2161    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292    0.1605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9757    0.9154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898    0.9839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4141    1.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2317    1.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5990    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0504    1.3896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4103    0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5190   -0.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815   -0.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9355   -0.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8268    0.6681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5541    1.1449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3808    0.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0643    0.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7747   -0.6939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2062   -0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3131   -0.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491   -0.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4215   -1.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -1.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0828   -1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8865   -2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0966    0.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655    0.5006    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7519   -0.6464    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2595   -1.3084    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0645   -1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695   -2.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8681   -0.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  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  1  0  0  0  0
 13 16  2  0  0  0  0
  9 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  6  0  0  0
 29 30  1  0  0  0  0
 27 31  1  0  0  0  0
  2 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341123

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CN3CCC4(O)C5=C(C=CC(OC)=C5)N=C4C(C1)(C(=O)OC)C3([H])[C@]([H])(CC)C2

> <INCHI_IDENTIFIER>
InChI=1S/C22H28N2O4/c1-4-14-9-13-11-21(20(25)28-3)18(14)24(12-13)8-7-22(26)16-10-15(27-2)5-6-17(16)23-19(21)22/h5-6,10,13-14,18,26H,4,7-9,11-12H2,1-3H3/t13-,14+,18?,21?,22?/m0/s1

> <INCHI_KEY>
AVRFPRAAVSCSSZ-GSEWTJHMSA-N

> <FORMULA>
C22H28N2O4

> <MOLECULAR_WEIGHT>
384.476

> <EXACT_MASS>
384.20490739

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.99451964703529

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (15S,17R)-17-ethyl-10-hydroxy-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2,4(9),5,7-tetraene-1-carboxylate

> <JCHEM_LOGP>
2.962146792333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.634026999764775

> <JCHEM_PKA_STRONGEST_BASIC>
8.867444189015577

> <JCHEM_POLAR_SURFACE_AREA>
71.36

> <JCHEM_REFRACTIVITY>
106.91019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (15S,17R)-17-ethyl-10-hydroxy-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2,4(9),5,7-tetraene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  H   UNK     0      -0.362   0.403   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.174   0.300   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.821   1.709   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       3.341   1.837   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.506   2.891   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.032   2.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.718   1.175   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.561   2.594   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.233   0.896   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.435  -0.631   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.859  -1.218   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.080  -0.279   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.877   1.247   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.234   2.137   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      13.778   1.809   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.453   1.835   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       7.046  -1.295   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       5.985  -0.179   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.318  -0.673   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.518  -0.627   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.520  -2.283   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.890  -3.220   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.755  -3.465   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.388  -4.961   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.914   0.377   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       5.349   0.934   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       3.270  -1.207   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0       2.351  -2.442   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0       3.854  -2.987   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.676  -4.650   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.620  -1.165   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20   31                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   18                                             
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13    9                                                       
CONECT   17   10   18                                                       
CONECT   18   17    7   19                                                  
CONECT   19   18   20   21   25                                             
CONECT   20   19    2                                                       
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   19    4   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28   29   31                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   27    2                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈N₂O₄

Average Molecular Weight

384.476

Monoisotopic Molecular Weight

384.20490739

IUPAC Name

methyl (15S,17R)-17-ethyl-10-hydroxy-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2,4(9),5,7-tetraene-1-carboxylate

Traditional Name

methyl (15S,17R)-17-ethyl-10-hydroxy-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2,4(9),5,7-tetraene-1-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@@]12CN3CCC4(O)C5=C(C=CC(OC)=C5)N=C4C(C1)(C(=O)OC)C3([H])[C@]([H])(CC)C2

InChI Identifier

InChI=1S/C22H28N2O4/c1-4-14-9-13-11-21(20(25)28-3)18(14)24(12-13)8-7-22(26)16-10-15(27-2)5-6-17(16)23-19(21)22/h5-6,10,13-14,18,26H,4,7-9,11-12H2,1-3H3/t13-,14+,18?,21?,22?/m0/s1

InChI Key

AVRFPRAAVSCSSZ-GSEWTJHMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ibogan-type alkaloids

Sub Class

Not Available

Direct Parent

Ibogan-type alkaloids

Alternative Parents

Substituents

Ibogan skeleton
Catharanthine skeleton
3-alkylindole
Indole or derivatives
Piperidinecarboxylic acid
Anisole
Phenol ether
Alkyl aryl ether
Azepane
Aralkylamine
Benzenoid
Piperidine
Methyl ester
Tertiary alcohol
Amino acid or derivatives
Carboxylic acid ester
Ketimine
Tertiary aliphatic amine
Tertiary amine
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Imine
Carbonyl group
Organic oxide
Organooxygen compound
Amine
Organonitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.96	ChemAxon
pKa (Strongest Acidic)	12.63	ChemAxon
pKa (Strongest Basic)	8.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.91 m³·mol⁻¹	ChemAxon
Polarizability	41.99 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 Retention Times

Not Available

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

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 Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

290705

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

328232

PDB ID

Not Available

ChEBI ID

Not Available

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

Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864 ]

Showing metabocard for 7alpha-Voacangine hydroxyindolenine (HMDB0341123)

MOL for HMDB0341123 (7alpha-Voacangine hydroxyindolenine)

3D MOL for HMDB0341123 (7alpha-Voacangine hydroxyindolenine)

3D SDF for HMDB0341123 (7alpha-Voacangine hydroxyindolenine)

3D-SDF for HMDB0341123 (7alpha-Voacangine hydroxyindolenine)

PDB for HMDB0341123 (7alpha-Voacangine hydroxyindolenine)

3D PDB for HMDB0341123 (7alpha-Voacangine hydroxyindolenine)

SMILES for HMDB0341123 (7alpha-Voacangine hydroxyindolenine)

INCHI for HMDB0341123 (7alpha-Voacangine hydroxyindolenine)

Structure for HMDB0341123 (7alpha-Voacangine hydroxyindolenine)

3D Structure for HMDB0341123 (7alpha-Voacangine hydroxyindolenine)

Predicted Retention Times

Predicted Kovats Retention Indices