NP-MRD: Showing NP-Card for 26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]hexacosa-3(15),4,6,12,25-pentaen-11-one (NP0186524)

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Record Information

Version

2.0

Created at

2022-09-04 02:24:38 UTC

Updated at

2022-09-04 02:24:38 UTC

NP-MRD ID

NP0186524

Secondary Accession Numbers

None

Natural Product Identification

Common Name

26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]hexacosa-3(15),4,6,12,25-pentaen-11-one

Description

26-Hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]Hexacosa-3(15),4(13),5,7(12),25-pentaen-11-one belongs to the class of organic compounds known as pyrroloquinolines. Pyrroloquinolines are compounds containing a pyrroloquinoline moiety, which consists of a pyrrole ring fused to a quinoline. 26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]hexacosa-3(15),4,6,12,25-pentaen-11-one is found in Penicillium herquei. Based on a literature review very few articles have been published on 26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]Hexacosa-3(15),4(13),5,7(12),25-pentaen-11-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042204242D          

 33 39  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042204242D          

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  7 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186524

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCN2CC34CC5=C(NC6=C7C(=O)CC(C)(C)OC7=CC=C56)C(C)(C)C3CC12C(O)=N4

> <INCHI_IDENTIFIER>
InChI=1S/C27H33N3O3/c1-14-8-9-30-13-26-10-16-15-6-7-18-20(17(31)11-24(2,3)33-18)21(15)28-22(16)25(4,5)19(26)12-27(14,30)23(32)29-26/h6-7,14,19,28H,8-13H2,1-5H3,(H,29,32)

> <INCHI_KEY>
MXLMYJLWDVPGLC-UHFFFAOYSA-N

> <FORMULA>
C27H33N3O3

> <MOLECULAR_WEIGHT>
447.579

> <EXACT_MASS>
447.252191935

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
51.41117801668105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0^{1,17}.0^{3,15}.0^{4,13}.0^{7,12}.0^{19,23}]hexacosa-3(15),4,6,12,25-pentaen-11-one

> <JCHEM_LOGP>
1.1270206648884715

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.989813164010744

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.299872826475253

> <JCHEM_PKA_STRONGEST_BASIC>
7.935375189516561

> <JCHEM_POLAR_SURFACE_AREA>
77.92

> <JCHEM_REFRACTIVITY>
126.69589999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0^{1,17}.0^{3,15}.0^{4,13}.0^{7,12}.0^{19,23}]hexacosa-3(15),4,6,12,25-pentaen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.623  -1.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.073   0.268   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.036   1.513   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.014   2.703   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.518   2.281   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.978   3.225   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.379   2.171   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.820   2.899   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.154   2.063   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.111   0.524   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       8.562   0.008   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.501   1.228   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.037   1.346   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.702   2.735   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.832   4.006   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.296   3.887   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.631   2.498   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.237   2.854   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.108   1.583   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.208   2.661   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.360   0.687   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.442   0.194   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.907   0.076   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.242  -1.313   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.828  -0.412   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.897  -1.520   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.876  -1.622   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.420   0.412   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.913  -0.450   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.507   0.558   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.971   0.724   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.140  -0.279   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0       2.917   2.121   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   28   33                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   25                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   23                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    9   12                                                  
CONECT   18   14   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23   22   13   24                                                  
CONECT   24   23                                                            
CONECT   25   10   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25    7   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29    2    5   31                                             
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    7                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₃N₃O₃

Average Mass

447.5790 Da

Monoisotopic Mass

447.25219 Da

IUPAC Name

26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0^{1,17}.0^{3,15}.0^{4,13}.0^{7,12}.0^{19,23}]hexacosa-3(15),4,6,12,25-pentaen-11-one

Traditional Name

26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0^{1,17}.0^{3,15}.0^{4,13}.0^{7,12}.0^{19,23}]hexacosa-3(15),4,6,12,25-pentaen-11-one

CAS Registry Number

Not Available

SMILES

CC1CCN2CC34CC5=C(NC6=C7C(=O)CC(C)(C)OC7=CC=C56)C(C)(C)C3CC12C(O)=N4

InChI Identifier

InChI=1S/C27H33N3O3/c1-14-8-9-30-13-26-10-16-15-6-7-18-20(17(31)11-24(2,3)33-18)21(15)28-22(16)25(4,5)19(26)12-27(14,30)23(32)29-26/h6-7,14,19,28H,8-13H2,1-5H3,(H,29,32)

InChI Key

MXLMYJLWDVPGLC-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Penicillium herquei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloquinolines. Pyrroloquinolines are compounds containing a pyrroloquinoline moiety, which consists of a pyrrole ring fused to a quinoline.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Pyrroloquinolines

Direct Parent

Pyrroloquinolines

Alternative Parents

Substituents

Pyrroloquinoline
Carbazole
2,2-dimethyl-1-benzopyran
Chromone
3-alkylindole
1-benzopyran
Benzopyran
Chromane
Indolizidine
Indole or derivatives
Indole
Aryl alkyl ketone
Aryl ketone
Aralkylamine
Tetrahydropyridine
Alkyl aryl ether
Benzenoid
N-alkylpyrrolidine
Piperidine
Heteroaromatic compound
Vinylogous amide
Cyclic carboximidic acid
Pyrrolidine
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Ketone
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
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	1.13	ChemAxon
pKa (Strongest Acidic)	2.3	ChemAxon
pKa (Strongest Basic)	7.94	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	126.7 m³·mol⁻¹	ChemAxon
Polarizability	51.41 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

162816138

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]hexacosa-3(15),4,6,12,25-pentaen-11-one (NP0186524)

MOL for NP0186524 (26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]hexacosa-3(15),4,6,12,25-pentaen-11-one)

3D MOL for NP0186524 (26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]hexacosa-3(15),4,6,12,25-pentaen-11-one)

3D SDF for NP0186524 (26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]hexacosa-3(15),4,6,12,25-pentaen-11-one)

3D-SDF for NP0186524 (26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]hexacosa-3(15),4,6,12,25-pentaen-11-one)

PDB for NP0186524 (26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]hexacosa-3(15),4,6,12,25-pentaen-11-one)

3D PDB for NP0186524 (26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]hexacosa-3(15),4,6,12,25-pentaen-11-one)

SMILES for NP0186524 (26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]hexacosa-3(15),4,6,12,25-pentaen-11-one)

INCHI for NP0186524 (26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]hexacosa-3(15),4,6,12,25-pentaen-11-one)

Structure for NP0186524 (26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]hexacosa-3(15),4,6,12,25-pentaen-11-one)

3D Structure for NP0186524 (26-hydroxy-9,9,16,16,20-pentamethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]hexacosa-3(15),4,6,12,25-pentaen-11-one)