NP-MRD: Showing NP-Card for Veratramine (NP0051308)

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Record Information

Version

2.0

Created at

2022-04-27 22:41:11 UTC

Updated at

2022-04-27 22:41:11 UTC

NP-MRD ID

NP0051308

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Veratramine

Description

Veratramine belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene. Veratramine is a very strong basic compound (based on its pKa). Veratramine is found in Apis cerana, Salvia sylvestris, Veratrum californicum, Veratrum dahuricum, Veratrum grandiflorum, Veratrum mengtzeanum, Veratrum mentzeanum, Veratrum nigrum , Veratrum patulum and Veratrum viride . Veratramine is a potentially toxic compound.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 08291401042D          

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M  END

     RDKit          3D

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  Mrv0541 08291401042D          

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 19 29  1  6  0  0  0
 25 30  1  1  0  0  0
 15 31  1  6  0  0  0
 17 32  1  6  0  0  0
 19 33  1  1  0  0  0
 22 34  1  6  0  0  0
 24 35  1  1  0  0  0
 25 36  1  6  0  0  0
 26 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051308

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](C)(C1=C(C)C2=C(C=C1)[C@]1([H])CC=C3C[C@@]([H])(O)CC[C@]3(C)[C@@]1([H])C2)[C@]1([H])NC[C@@]([H])(C)C[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C27H39NO2/c1-15-11-25(30)26(28-14-15)17(3)20-7-8-21-22-6-5-18-12-19(29)9-10-27(18,4)24(22)13-23(21)16(20)2/h5,7-8,15,17,19,22,24-26,28-30H,6,9-14H2,1-4H3/t15-,17-,19-,22-,24-,25+,26-,27-/m0/s1

> <INCHI_KEY>
MALFODICFSIXPO-KFKQDBFTSA-N

> <FORMULA>
C27H39NO2

> <MOLECULAR_WEIGHT>
409.6041

> <EXACT_MASS>
409.298079497

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.65718001457323

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,5S)-2-[(1S)-1-[(1S,2R,5S,10R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-7,11(16),12,14-tetraen-14-yl]ethyl]-5-methylpiperidin-3-ol

> <ALOGPS_LOGP>
4.57

> <JCHEM_LOGP>
4.41318638

> <ALOGPS_LOGS>
-5.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.204289255855077

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.57388006587033

> <JCHEM_PKA_STRONGEST_BASIC>
9.913187751691336

> <JCHEM_POLAR_SURFACE_AREA>
52.489999999999995

> <JCHEM_REFRACTIVITY>
124.08889999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.95e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
veratramine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0      16.028   2.689   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.254  -2.307   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.919  -2.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.564  -0.694   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.024   3.345   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.561   3.257   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.404   1.603   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.035   2.308   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.489  -0.517   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.026  -0.606   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.805   0.318   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.641   2.146   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.372  -0.607   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.363   2.562   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.732   1.856   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.181  -0.768   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.845  -0.641   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.179   2.057   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.204   0.858   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.477   0.064   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.739   1.476   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.254   1.881   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.812  -0.063   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.409   0.594   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.510  -0.515   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.141   0.191   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.871   0.682   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      12.068   1.729   0.000  0.00  0.00           N+0
HETATM   29  O   UNK     0      -1.741   0.946   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      13.583  -2.053   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0      14.659   3.394   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       9.550  -1.474   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.896   2.234   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       6.229   3.074   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.716   1.969   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      12.214  -1.347   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0      10.772   0.897   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   27                                                            
CONECT    5    6   18                                                       
CONECT    6    5   22                                                       
CONECT    7    8   20                                                       
CONECT    8    7   21                                                       
CONECT    9   10   19                                                       
CONECT   10    9   27                                                       
CONECT   11   15   25                                                       
CONECT   12   18   19                                                       
CONECT   13   23   24                                                       
CONECT   14   15   28                                                       
CONECT   15    1   11   14   31                                             
CONECT   16    2   20   23                                                  
CONECT   17    3   20   26   32                                             
CONECT   18    5   12   27                                                  
CONECT   19    9   12   29   33                                             
CONECT   20    7   16   17                                                  
CONECT   21    8   22   23                                                  
CONECT   22    6   21   24   34                                             
CONECT   23   13   16   21                                                  
CONECT   24   13   22   27   35                                             
CONECT   25   11   26   30   36                                             
CONECT   26   17   25   28   37                                             
CONECT   27    4   10   18   24                                             
CONECT   28   14   26                                                       
CONECT   29   19                                                            
CONECT   30   25                                                            
CONECT   31   15                                                            
CONECT   32   17                                                            
CONECT   33   19                                                            
CONECT   34   22                                                            
CONECT   35   24                                                            
CONECT   36   25                                                            
CONECT   37   26                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
(3beta,23beta)-14,15,16,17-Tetradehydroveratraman-3,23-diol	ChEBI
(3b,23b)-14,15,16,17-Tetradehydroveratraman-3,23-diol	Generator
(3Β,23β)-14,15,16,17-tetradehydroveratraman-3,23-diol	Generator
5-Methyl-2-(1-(2,3,4,6,6a,11,11a,11b-octahydro- 3-hydroxy-10,11b-dimethyl-1H-benzo(a)fluoren-9- yl)ethyl)piperidin-3-ol	MeSH
Veratramin	MeSH

Chemical Formula

C₂₇H₃₉NO₂

Average Mass

409.6041 Da

Monoisotopic Mass

409.29808 Da

IUPAC Name

(2S,3R,5S)-2-[(1S)-1-[(1S,2R,5S,10R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-7,11(16),12,14-tetraen-14-yl]ethyl]-5-methylpiperidin-3-ol

Traditional Name

veratramine

CAS Registry Number

Not Available

SMILES

[H][C@](C)(C1=C(C)C2=C(C=C1)[C@]1([H])CC=C3C[C@@]([H])(O)CC[C@]3(C)[C@@]1([H])C2)[C@]1([H])NC[C@@]([H])(C)C[C@@]1([H])O

InChI Identifier

InChI=1S/C27H39NO2/c1-15-11-25(30)26(28-14-15)17(3)20-7-8-21-22-6-5-18-12-19(29)9-10-27(18,4)24(22)13-23(21)16(20)2/h5,7-8,15,17,19,22,24-26,28-30H,6,9-14H2,1-4H3/t15-,17-,19-,22-,24-,25+,26-,27-/m0/s1

InChI Key

MALFODICFSIXPO-KFKQDBFTSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Salvia x sylvestris	LOTUS Database	35616633
Veratrum californicum	LOTUS Database	35616633
Veratrum dahuricum	Plant	KNApSAcK
Veratrum grandiflorum	Plant	KNApSAcK
Veratrum mengtzeanum	LOTUS Database	35616633
Veratrum mentzeanum	Plant	KNApSAcK
Veratrum nigrum	Plant	KNApSAcK
Veratrum patulum	Plant	KNApSAcK
Veratrum viride	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Fluorenes

Sub Class

Not Available

Direct Parent

Fluorenes

Alternative Parents

Substituents

Fluorene
Indane
Aralkylamine
Piperidine
Cyclic alcohol
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Azacycle
Organoheterocyclic compound
Secondary amine
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

piperidine alkaloid (CHEBI:9951 )
Steroidal alkaloids (C10829 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.57	ALOGPS
logP	4.41	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	14.57	ChemAxon
pKa (Strongest Basic)	9.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	52.49 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	124.09 m³·mol⁻¹	ChemAxon
Polarizability	49.66 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002270

Chemspider ID

Not Available

KEGG Compound ID

C10829

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Veratramine

METLIN ID

Not Available

PubChem Compound

6070

PDB ID

Not Available

ChEBI ID

9951

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Veratramine (NP0051308)

MOL for NP0051308 (Veratramine)

3D MOL for NP0051308 (Veratramine)

3D SDF for NP0051308 (Veratramine)

3D-SDF for NP0051308 (Veratramine)

PDB for NP0051308 (Veratramine)

3D PDB for NP0051308 (Veratramine)

SMILES for NP0051308 (Veratramine)

INCHI for NP0051308 (Veratramine)

Structure for NP0051308 (Veratramine)

3D Structure for NP0051308 (Veratramine)