NP-MRD: Showing NP-Card for Protoverine (NP0051303)

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Record Information

Version

2.0

Created at

2022-04-27 22:40:52 UTC

Updated at

2022-04-27 22:40:52 UTC

NP-MRD ID

NP0051303

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Protoverine

Description

Protoverine belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids. Protoverine is found in Veratrum album and Veratrum lobelianum Bernh. . Based on a literature review very few articles have been published on Protoverine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200402D          

 37 43  0  0  1  0            999 V2000
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  5 35  1  1  0  0  0
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  2 37  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282200402D          

 37 43  0  0  1  0            999 V2000
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    4.6937   -3.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3348   -2.6892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6779   -3.1683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1500   -0.8484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3511   -0.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8673   -2.0962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7804   -0.4008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
  9 12  1  6  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
  7 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  6  0  0  0
 18 21  1  1  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 16 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 27 30  1  1  0  0  0
 22 31  1  6  0  0  0
 22 32  1  1  0  0  0
 13 33  1  6  0  0  0
  7 34  1  6  0  0  0
  3 34  1  0  0  0  0
  5 35  1  1  0  0  0
  3 36  1  6  0  0  0
  2 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051303

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@@H]2N(C1)C[C@H]1[C@@H]3C[C@@]45O[C@@]6(O)[C@@H]([C@@H](O)[C@@H](O)[C@H]4[C@]3(O)[C@@H](O)[C@H](O)[C@@H]1[C@]2(C)O)[C@]5(C)CC[C@@H]6O

> <INCHI_IDENTIFIER>
InChI=1S/C27H43NO9/c1-11-4-5-14-24(3,34)16-12(10-28(14)9-11)13-8-25-21(26(13,35)22(33)17(16)30)19(32)18(31)20-23(25,2)7-6-15(29)27(20,36)37-25/h11-22,29-36H,4-10H2,1-3H3/t11-,12-,13-,14-,15-,16+,17+,18-,19+,20-,21+,22-,23-,24+,25+,26-,27+/m0/s1

> <INCHI_KEY>
CKJAABZFXLMMCS-MKKPLVDTSA-N

> <FORMULA>
C27H43NO9

> <MOLECULAR_WEIGHT>
525.639

> <EXACT_MASS>
525.293781969

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.31228670992167

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,16S,17R,18R,19S,22S,23S,25R)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosan-10,12,13,14,16,17,22,23-octol

> <ALOGPS_LOGP>
-0.25

> <JCHEM_LOGP>
-2.320257646666666

> <ALOGPS_LOGS>
-1.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.67686194488855

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.831221885848773

> <JCHEM_PKA_STRONGEST_BASIC>
7.971165099554576

> <JCHEM_POLAR_SURFACE_AREA>
174.30999999999997

> <JCHEM_REFRACTIVITY>
128.9791

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.56e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,16S,17R,18R,19S,22S,23S,25R)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosan-10,12,13,14,16,17,22,23-octol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.656  -0.016   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.814  -1.055   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.166  -2.441   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.117  -3.277   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.190  -1.981   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.861  -0.401   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.026  -2.722   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.488  -4.322   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.382  -5.377   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.041  -4.849   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.284  -5.759   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.693  -6.885   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.989  -4.634   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.660  -3.249   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.530  -2.169   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.196  -3.137   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.061  -4.412   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.389  -5.798   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.853  -5.909   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.182  -7.295   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       7.254  -7.072   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.597  -4.300   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.268  -2.914   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       8.404  -1.640   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       6.868  -1.751   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.075  -0.254   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.611  -0.143   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.476  -1.417   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.804  -2.803   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.283   1.243   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.762  -5.831   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.958  -5.020   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.132  -5.914   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.280  -1.584   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.522  -1.209   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.619  -3.913   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -3.323  -0.748   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   37                                                  
CONECT    3    2    4   34   36                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   35                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   15   34                                             
CONECT    8    7    9   13                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9                                                            
CONECT   13    8   14   19   33                                             
CONECT   14   13   15   16                                                  
CONECT   15   14    7                                                       
CONECT   16   14   17   25                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   13   20                                                  
CONECT   20   19                                                            
CONECT   21   18                                                            
CONECT   22   17   23   31   32                                             
CONECT   23   22   24   29                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   16                                                       
CONECT   26   24   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28   23                                                       
CONECT   30   27                                                            
CONECT   31   22                                                            
CONECT   32   22                                                            
CONECT   33   13                                                            
CONECT   34    7    3                                                       
CONECT   35    5                                                            
CONECT   36    3                                                            
CONECT   37    2                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Value	Source
Protoverine, monohydrochloride, (3beta,4alpha,6alpha,7alpha,15alpha,16beta)-isomer	MeSH

Chemical Formula

C₂₇H₄₃NO₉

Average Mass

525.6390 Da

Monoisotopic Mass

525.29378 Da

IUPAC Name

(1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,16S,17R,18R,19S,22S,23S,25R)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosan-10,12,13,14,16,17,22,23-octol

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@@H]2N(C1)C[C@H]1[C@@H]3C[C@@]45O[C@@]6(O)[C@@H]([C@@H](O)[C@@H](O)[C@H]4[C@]3(O)[C@@H](O)[C@H](O)[C@@H]1[C@]2(C)O)[C@]5(C)CC[C@@H]6O

InChI Identifier

InChI=1S/C27H43NO9/c1-11-4-5-14-24(3,34)16-12(10-28(14)9-11)13-8-25-21(26(13,35)22(33)17(16)30)19(32)18(31)20-23(25,2)7-6-15(29)27(20,36)37-25/h11-22,29-36H,4-10H2,1-3H3/t11-,12-,13-,14-,15-,16+,17+,18-,19+,20-,21+,22-,23-,24+,25+,26-,27+/m0/s1

InChI Key

CKJAABZFXLMMCS-MKKPLVDTSA-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
Veratrum album	Plant	KNApSAcK
Veratrum lobelianum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Cerveratrum-type alkaloids

Alternative Parents

Substituents

Cerveratrum-type alkaloid
Azasteroid
Quinolizidine
Alkaloid or derivatives
Oxepane
Piperidine
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Tertiary amine
Secondary alcohol
Tertiary aliphatic amine
1,2-aminoalcohol
Hemiacetal
Azacycle
Organoheterocyclic compound
Oxacycle
Alcohol
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:8596 )
Steroidal alkaloids (C10817 )

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	-0.25	ALOGPS
logP	-2.3	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	10.83	ChemAxon
pKa (Strongest Basic)	7.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	174.31 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	128.98 m³·mol⁻¹	ChemAxon
Polarizability	55.31 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00002258

Chemspider ID

391285

KEGG Compound ID

C10817

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442982

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1500651

References

General References

Not Available

Showing NP-Card for Protoverine (NP0051303)

MOL for NP0051303 (Protoverine)

3D MOL for NP0051303 (Protoverine)

3D SDF for NP0051303 (Protoverine)

3D-SDF for NP0051303 (Protoverine)

PDB for NP0051303 (Protoverine)

3D PDB for NP0051303 (Protoverine)

SMILES for NP0051303 (Protoverine)

INCHI for NP0051303 (Protoverine)

Structure for NP0051303 (Protoverine)

3D Structure for NP0051303 (Protoverine)