NP-MRD: Showing NP-Card for 19beta-Hydroxyvenalstonidine (NP0066844)

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Record Information

Version

2.0

Created at

2022-04-28 11:04:57 UTC

Updated at

2022-04-28 11:04:57 UTC

NP-MRD ID

NP0066844

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19beta-Hydroxyvenalstonidine

Description

Methyl (1R,2R,4R,9S,17S,18R,20R,22S)-20-hydroxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]Docosa-10,12,14-triene-18-carboxylate belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond. 19beta-Hydroxyvenalstonidine is found in Melodinus insulae-pinorum Boiteau. and Melodinus reticulatus. Based on a literature review very few articles have been published on methyl (1R,2R,4R,9S,17S,18R,20R,22S)-20-hydroxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]Docosa-10,12,14-triene-18-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282213042D          

 27 33  0  0  1  0            999 V2000
    8.7231   -0.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2860    0.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0451    1.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2413    1.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6784    0.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9193   -0.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7955    0.8392    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0041    1.7715    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8030    2.1136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2503    2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3287    2.1721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0953    1.2692    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8391    0.6815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6567   -0.1956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8314   -0.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855    0.1653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2587    0.9870    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5104    0.6395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3507   -0.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8758   -0.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7245    1.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3814    1.3443    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3586    0.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4326    0.3547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2616    0.2068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4486   -0.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6404    2.7569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 16 18  1  1  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 12 21  1  6  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 11 27  1  6  0  0  0
M  END


  Mrv1652304282213042D          

 27 33  0  0  1  0            999 V2000
    8.7231   -0.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2860    0.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0451    1.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2413    1.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6784    0.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9193   -0.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7955    0.8392    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0041    1.7715    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8030    2.1136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2503    2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3287    2.1721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0953    1.2692    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8391    0.6815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6567   -0.1956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8314   -0.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855    0.1653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2587    0.9870    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5104    0.6395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3507   -0.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8758   -0.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7245    1.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3814    1.3443    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3586    0.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4326    0.3547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2616    0.2068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4486   -0.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6404    2.7569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 16 18  1  1  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 12 21  1  6  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 11 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0066844

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1C[C@@]23[C@H]4O[C@@H]4CN4CC[C@@]5([C@@H]24)C2=CC=CC=C2N[C@@]15C[C@H]3O

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O4/c1-26-17(25)12-8-19-15(24)9-21(12)20(11-4-2-3-5-13(11)22-21)6-7-23(18(19)20)10-14-16(19)27-14/h2-5,12,14-16,18,22,24H,6-10H2,1H3/t12-,14+,15+,16-,18+,19+,20-,21-/m0/s1

> <INCHI_KEY>
HNUOJNHAJOCKBT-FQFMQGSZSA-N

> <FORMULA>
C21H24N2O4

> <MOLECULAR_WEIGHT>
368.433

> <EXACT_MASS>
368.173607261

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.59406617194422

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2R,4R,9S,17S,18R,20R,22S)-20-hydroxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1^{1,6}.0^{2,4}.0^{9,17}.0^{10,15}.0^{9,22}]docosa-10,12,14-triene-18-carboxylate

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
0.15078762100000015

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.578373317346635

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.505818436909358

> <JCHEM_PKA_STRONGEST_BASIC>
8.736759733502154

> <JCHEM_POLAR_SURFACE_AREA>
74.33

> <JCHEM_REFRACTIVITY>
97.5673

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2R,4R,9S,17S,18R,20R,22S)-20-hydroxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1^{1,6}.0^{2,4}.0^{9,17}.0^{10,15}.0^{9,22}]docosa-10,12,14-triene-18-carboxylate

> <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      16.283  -0.358   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.334   0.768   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.884   2.241   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.384   2.588   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.333   1.462   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.783  -0.011   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.685   1.567   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.074   3.307   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      14.566   3.945   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      11.667   4.301   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.947   4.055   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.511   2.369   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.900   1.272   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      10.559  -0.365   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       9.019  -0.688   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.813   0.309   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.949   1.842   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.553   1.194   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.855  -1.259   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.835  -0.035   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.686   3.213   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.912   2.509   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.869   0.898   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.141   0.662   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      13.555   0.386   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.904  -1.114   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.662   5.146   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   13   20                                             
CONECT    8    7    9   10   22                                             
CONECT    9    8    4                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   27                                                  
CONECT   12   11   13   17   21                                             
CONECT   13   12    7   14                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17   16                                                       
CONECT   19   14   20                                                       
CONECT   20   19    7                                                       
CONECT   21   12   22                                                       
CONECT   22   21    8   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   11                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   66    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,2R,4R,9S,17S,18R,20R,22S)-20-hydroxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1,.0,.0,.0,.0,]docosa-10,12,14-triene-18-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₄N₂O₄

Average Mass

368.4330 Da

Monoisotopic Mass

368.17361 Da

IUPAC Name

methyl (1R,2R,4R,9S,17S,18R,20R,22S)-20-hydroxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1^{1,6}.0^{2,4}.0^{9,17}.0^{10,15}.0^{9,22}]docosa-10,12,14-triene-18-carboxylate

Traditional Name

methyl (1R,2R,4R,9S,17S,18R,20R,22S)-20-hydroxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1^{1,6}.0^{2,4}.0^{9,17}.0^{10,15}.0^{9,22}]docosa-10,12,14-triene-18-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1C[C@@]23[C@H]4O[C@@H]4CN4CC[C@@]5([C@@H]24)C2=CC=CC=C2N[C@@]15C[C@H]3O

InChI Identifier

InChI=1S/C21H24N2O4/c1-26-17(25)12-8-19-15(24)9-21(12)20(11-4-2-3-5-13(11)22-21)6-7-23(18(19)20)10-14-16(19)27-14/h2-5,12,14-16,18,22,24H,6-10H2,1H3/t12-,14+,15+,16-,18+,19+,20-,21-/m0/s1

InChI Key

HNUOJNHAJOCKBT-FQFMQGSZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melodinus insulae-pinorum Boiteau.	Plant	KNApSAcK
Melodinus reticulatus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidofractine alkaloids

Sub Class

Not Available

Direct Parent

Aspidofractine alkaloids

Alternative Parents

Substituents

Aspidofractine skeleton
Aspidosperma alkaloid
Carbazole
Quinolidine
Azaspirodecane
Indolizidine
Dihydroindole
Indole or derivatives
Aralkylamine
Secondary aliphatic/aromatic amine
Epoxypiperidine
Para-oxazepine
Benzenoid
N-alkylpyrrolidine
Piperidine
Methyl ester
Pyrrolidine
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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
logP	1.51	ALOGPS
logP	0.15	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	14.51	ChemAxon
pKa (Strongest Basic)	8.74	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.33 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.57 m³·mol⁻¹	ChemAxon
Polarizability	38.59 Å³	ChemAxon
Number of Rings	7	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163019159

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 19beta-Hydroxyvenalstonidine (NP0066844)

MOL for NP0066844 (19beta-Hydroxyvenalstonidine)

3D MOL for NP0066844 (19beta-Hydroxyvenalstonidine)

3D SDF for NP0066844 (19beta-Hydroxyvenalstonidine)

3D-SDF for NP0066844 (19beta-Hydroxyvenalstonidine)

PDB for NP0066844 (19beta-Hydroxyvenalstonidine)

3D PDB for NP0066844 (19beta-Hydroxyvenalstonidine)

SMILES for NP0066844 (19beta-Hydroxyvenalstonidine)

INCHI for NP0066844 (19beta-Hydroxyvenalstonidine)

Structure for NP0066844 (19beta-Hydroxyvenalstonidine)

3D Structure for NP0066844 (19beta-Hydroxyvenalstonidine)