NP-MRD: Showing NP-Card for (21s)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6-trien-9-one (NP0255338)

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Record Information

Version

2.0

Created at

2022-09-07 19:48:03 UTC

Updated at

2022-09-07 19:48:03 UTC

NP-MRD ID

NP0255338

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(21s)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6-trien-9-one

Description

(21S)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]Henicosa-2,4,6-trien-9-one belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton. (21s)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6-trien-9-one is found in Strychnos icaja. Based on a literature review very few articles have been published on (21S)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]Henicosa-2,4,6-trien-9-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072221482D          

 26 31  0  0  1  0            999 V2000
    3.3832    3.5751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0960    3.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8121    3.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5396    3.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2361    3.6330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5883    2.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4053    1.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0210    1.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5219    0.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9471    0.1831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2424   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5519    0.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7363    1.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8641    0.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    0.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944    0.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159    1.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6615    1.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4856    1.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771    2.3208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.9295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7898    0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0102    1.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8119    1.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3812    0.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1830    1.0638    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  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  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  1  0  0  0  0
 12 13  1  0  0  0  0
  9 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
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 21 20  1  1  0  0  0
  6 21  1  0  0  0  0
 13 21  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END


  Mrv1652309072221482D          

 26 31  0  0  1  0            999 V2000
    3.3832    3.5751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0960    3.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8121    3.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5396    3.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2361    3.6330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5883    2.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4053    1.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0210    1.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5219    0.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9471    0.1831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2424   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5519    0.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7363    1.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8641    0.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    0.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944    0.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159    1.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6615    1.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4856    1.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771    2.3208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.9295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7898    0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0102    1.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8119    1.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3812    0.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1830    1.0638    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  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  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  1  0  0  0  0
 12 13  1  0  0  0  0
  9 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
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 21 20  1  1  0  0  0
  6 21  1  0  0  0  0
 13 21  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255338

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCC1CN2CCC34C2CC1C1[C@@H]3N(C2=CC=CC=C42)C(=O)CC1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O3/c24-8-5-12-11-22-7-6-21-14-3-1-2-4-15(14)23-18(26)10-16(25)19(20(21)23)13(12)9-17(21)22/h1-4,12-13,16-17,19-20,24-25H,5-11H2/t12?,13?,16?,17?,19?,20-,21?/m0/s1

> <INCHI_KEY>
SBHBRKPHBFFIFF-WDJNYBRMSA-N

> <FORMULA>
C21H26N2O3

> <MOLECULAR_WEIGHT>
354.45

> <EXACT_MASS>
354.194342705

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.7946196484077

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(21S)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1^{1,8}.0^{2,7}.0^{16,19}.0^{12,21}]henicosa-2,4,6-trien-9-one

> <JCHEM_LOGP>
-0.06346394533333374

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.983735906791669

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.638255328160845

> <JCHEM_PKA_STRONGEST_BASIC>
9.803407385606262

> <JCHEM_POLAR_SURFACE_AREA>
64.01

> <JCHEM_REFRACTIVITY>
97.39880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(21S)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1^{1,8}.0^{2,7}.0^{16,19}.0^{12,21}]henicosa-2,4,6-trien-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       6.315   6.674   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.646   5.898   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.983   6.696   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.341   5.956   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.641   6.782   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.432   4.420   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.957   3.646   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.239   2.750   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.308   1.594   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      11.101   0.342   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       9.786  -0.591   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.497   0.333   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.841   1.959   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.213   1.839   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.381   0.543   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.843   0.616   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.136   1.984   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.968   3.280   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.506   3.208   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       7.611   4.332   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       8.978   3.602   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.674   0.765   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.086   2.374   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.582   2.737   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.645   1.623   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      17.142   1.986   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   21                                                  
CONECT    7    6    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9   14   21                                             
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19    2   21                                                  
CONECT   21   20    6   13                                                  
CONECT   22   10   23                                                       
CONECT   23   22    7   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆N₂O₃

Average Mass

354.4500 Da

Monoisotopic Mass

354.19434 Da

IUPAC Name

(21S)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1^{1,8}.0^{2,7}.0^{16,19}.0^{12,21}]henicosa-2,4,6-trien-9-one

Traditional Name

(21S)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1^{1,8}.0^{2,7}.0^{16,19}.0^{12,21}]henicosa-2,4,6-trien-9-one

CAS Registry Number

Not Available

SMILES

OCCC1CN2CCC34C2CC1C1[C@@H]3N(C2=CC=CC=C42)C(=O)CC1O

InChI Identifier

InChI=1S/C21H26N2O3/c24-8-5-12-11-22-7-6-21-14-3-1-2-4-15(14)23-18(26)10-16(25)19(20(21)23)13(12)9-17(21)22/h1-4,12-13,16-17,19-20,24-25H,5-11H2/t12?,13?,16?,17?,19?,20-,21?/m0/s1

InChI Key

SBHBRKPHBFFIFF-WDJNYBRMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Strychnos icaja	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Strychnos alkaloids

Sub Class

Not Available

Direct Parent

Strychnos alkaloids

Alternative Parents

Substituents

Strychnan skeleton
Akuammicine-skeleton
Stemmadenine-skeleton
Carbazole
Quinolidine
Indole or derivatives
Indolizidine
Delta-lactam
Piperidinone
Aralkylamine
Piperidine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Tertiary aliphatic amine
Secondary alcohol
Tertiary amine
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Alcohol
Primary 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	-0.063	ChemAxon
pKa (Strongest Acidic)	14.64	ChemAxon
pKa (Strongest Basic)	9.8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.01 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.4 m³·mol⁻¹	ChemAxon
Polarizability	38.79 Å³	ChemAxon
Number of Rings	6	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

4478740

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320746

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (21s)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6-trien-9-one (NP0255338)

MOL for NP0255338 ((21s)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6-trien-9-one)

3D MOL for NP0255338 ((21s)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6-trien-9-one)

3D SDF for NP0255338 ((21s)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6-trien-9-one)

3D-SDF for NP0255338 ((21s)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6-trien-9-one)

PDB for NP0255338 ((21s)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6-trien-9-one)

3D PDB for NP0255338 ((21s)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6-trien-9-one)

SMILES for NP0255338 ((21s)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6-trien-9-one)

INCHI for NP0255338 ((21s)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6-trien-9-one)

Structure for NP0255338 ((21s)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6-trien-9-one)

3D Structure for NP0255338 ((21s)-11-hydroxy-14-(2-hydroxyethyl)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6-trien-9-one)