NP-MRD: Showing NP-Card for (16s)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one (NP0328265)

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Record Information

Version

2.0

Created at

2022-09-12 11:35:08 UTC

Updated at

2022-09-12 11:35:09 UTC

NP-MRD ID

NP0328265

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(16s)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one

Description

(16S)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]Henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. (16s)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one is found in Nauclea diderrichii. Based on a literature review very few articles have been published on (16S)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]Henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122213352D          

 23 26  0  0  1  0            999 V2000
    6.4244    1.9282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9306    0.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7374    0.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2901    0.1519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0361   -0.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2706   -0.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8243   -0.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7486   -1.6373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9586   -2.4352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9797   -1.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1223   -1.6212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4835   -1.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6843   -0.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3876    0.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5202    0.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7868    1.1994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2009    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3772    0.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9248   -0.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2962   -0.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1198   -0.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5722   -0.1181    0.0000 C   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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  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
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 15 23  1  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328265

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CNCCC2=C(NC3=CC=CC=C23)C(=O)C2=CN=CC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C18H17N3O2/c22-16-10-19-6-5-14-13-3-1-2-4-15(13)21-17(14)18(23)12-7-11(16)8-20-9-12/h1-4,7-9,16,19,21-22H,5-6,10H2/t16-/m1/s1

> <INCHI_KEY>
VHXXSFCTDCAIPR-MRXNPFEDSA-N

> <FORMULA>
C18H17N3O2

> <MOLECULAR_WEIGHT>
307.353

> <EXACT_MASS>
307.132076799

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.09728822888985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(16S)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0^{3,11}.0^{5,10}]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one

> <JCHEM_LOGP>
1.2015919370000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.891758559653962

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.198996028020673

> <JCHEM_PKA_STRONGEST_BASIC>
8.092615001771613

> <JCHEM_POLAR_SURFACE_AREA>
78.00999999999999

> <JCHEM_REFRACTIVITY>
87.96070000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(16S)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0^{3,11}.0^{5,10}]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0      11.992   3.599   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.745   2.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.937   1.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.443   1.427   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      15.475   0.284   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      15.001  -1.182   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.572  -1.864   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.739  -0.569   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.597  -3.056   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.989  -4.546   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.162  -2.498   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       9.562  -3.026   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       8.369  -2.052   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.744  -0.709   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.057   0.014   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.304   1.534   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       8.935   2.239   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       7.842   1.155   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.304   1.242   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.460  -0.046   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.153  -1.421   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.690  -1.508   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.535  -0.220   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   15   18                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₇N₃O₂

Average Mass

307.3530 Da

Monoisotopic Mass

307.13208 Da

IUPAC Name

(16S)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0^{3,11}.0^{5,10}]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one

Traditional Name

(16S)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0^{3,11}.0^{5,10}]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one

CAS Registry Number

Not Available

SMILES

O[C@@H]1CNCCC2=C(NC3=CC=CC=C23)C(=O)C2=CN=CC1=C2

InChI Identifier

InChI=1S/C18H17N3O2/c22-16-10-19-6-5-14-13-3-1-2-4-15(13)21-17(14)18(23)12-7-11(16)8-20-9-12/h1-4,7-9,16,19,21-22H,5-6,10H2/t16-/m1/s1

InChI Key

VHXXSFCTDCAIPR-MRXNPFEDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Nauclea diderrichii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids and derivatives

Alternative Parents

Substituents

Indolecarboxylic acid derivative
3-alkylindole
Indole
Aryl ketone
Aralkylamine
Pyridine
Benzenoid
Pyrrole
Heteroaromatic compound
1,2-aminoalcohol
Ketone
Secondary alcohol
Secondary aliphatic amine
Secondary amine
Azacycle
Amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
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	1.2	ChemAxon
pKa (Strongest Acidic)	13.2	ChemAxon
pKa (Strongest Basic)	8.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.01 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.96 m³·mol⁻¹	ChemAxon
Polarizability	32.1 Å³	ChemAxon
Number of Rings	4	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

162954836

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (16s)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one (NP0328265)

MOL for NP0328265 ((16s)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one)

3D MOL for NP0328265 ((16s)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one)

3D SDF for NP0328265 ((16s)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one)

3D-SDF for NP0328265 ((16s)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one)

PDB for NP0328265 ((16s)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one)

3D PDB for NP0328265 ((16s)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one)

SMILES for NP0328265 ((16s)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one)

INCHI for NP0328265 ((16s)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one)

Structure for NP0328265 ((16s)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one)

3D Structure for NP0328265 ((16s)-16-hydroxy-4,14,19-triazatetracyclo[15.3.1.0³,¹¹.0⁵,¹⁰]henicosa-1(20),3(11),5,7,9,17(21),18-heptaen-2-one)