NP-MRD: Showing NP-Card for 2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-8'-one (NP0302638)

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Record Information

Version

2.0

Created at

2022-09-10 16:21:28 UTC

Updated at

2022-09-10 16:21:28 UTC

NP-MRD ID

NP0302638

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-8'-one

Description

2,6',13'-Trihydroxy-4',4',7,7-tetramethyl-7H-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]Tetradecan]-13'-en-8'-one belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-8'-one is found in Aspergillus sclerotiorum. Based on a literature review very few articles have been published on 2,6',13'-trihydroxy-4',4',7,7-tetramethyl-7H-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]Tetradecan]-13'-en-8'-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102218212D          

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M  END

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M  END


  Mrv1652309102218212D          

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M  END
> <DATABASE_ID>
NP0302638

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2CC34CCCN3C(=O)C2(N=C4O)C(O)C11C(O)=NC2=C1C=CC1=C2C=CC(C)(C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C26H29N3O5/c1-22(2)10-8-13-15(34-22)7-6-14-17(13)27-20(32)25(14)18(30)26-16(23(25,3)4)12-24(19(31)28-26)9-5-11-29(24)21(26)33/h6-8,10,16,18,30H,5,9,11-12H2,1-4H3,(H,27,32)(H,28,31)

> <INCHI_KEY>
CFJMAERFDLWMJL-UHFFFAOYSA-N

> <FORMULA>
C26H29N3O5

> <MOLECULAR_WEIGHT>
463.534

> <EXACT_MASS>
463.210721046

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
49.56155421335547

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6',13'-trihydroxy-4',4',7,7-tetramethyl-7H-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-en-8'-one

> <JCHEM_LOGP>
2.6704833693333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.274216091603839

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6093341282078675

> <JCHEM_PKA_STRONGEST_BASIC>
0.5956645177704972

> <JCHEM_POLAR_SURFACE_AREA>
114.95

> <JCHEM_REFRACTIVITY>
125.90429999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-en-8'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      19.759   1.876   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.254   2.205   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.839   3.629   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.191   0.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.827  -0.049   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.526   0.775   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.589   2.314   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.288   3.138   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.924   2.423   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.861   0.884   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.162   0.060   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      13.781  -1.432   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      12.244  -1.530   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.420  -2.831   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.675  -0.099   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.428  -1.051   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.572  -2.585   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.996  -0.334   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       7.626   0.164   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       8.069   1.499   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.453   2.175   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.688   1.990   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.313   2.785   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.033   1.885   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.637   0.438   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       6.233   0.351   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       7.373  -0.942   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.999  -2.436   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.291   2.613   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.445   1.315   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.043   1.334   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.150   2.870   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.398   2.067   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      16.953   3.029   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   34                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   34                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   10   16   31                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   27   30                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   26   29                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22   27                                                  
CONECT   27   26   18   28                                                  
CONECT   28   27                                                            
CONECT   29   22   30                                                       
CONECT   30   29   18   31                                                  
CONECT   31   30   15   32   33                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    7    2                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₉N₃O₅

Average Mass

463.5340 Da

Monoisotopic Mass

463.21072 Da

IUPAC Name

2,6',13'-trihydroxy-4',4',7,7-tetramethyl-7H-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-en-8'-one

Traditional Name

2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-en-8'-one

CAS Registry Number

Not Available

SMILES

CC1(C)C2CC34CCCN3C(=O)C2(N=C4O)C(O)C11C(O)=NC2=C1C=CC1=C2C=CC(C)(C)O1

InChI Identifier

InChI=1S/C26H29N3O5/c1-22(2)10-8-13-15(34-22)7-6-14-17(13)27-20(32)25(14)18(30)26-16(23(25,3)4)12-24(19(31)28-26)9-5-11-29(24)21(26)33/h6-8,10,16,18,30H,5,9,11-12H2,1-4H3,(H,27,32)(H,28,31)

InChI Key

CFJMAERFDLWMJL-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
Aspergillus sclerotiorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
3-alkylindole
Alpha-amino acid or derivatives
Indolizidine
Indole or derivatives
Piperidinone
Tetrahydropyridine
Alkyl aryl ether
Delta-lactam
Piperidine
Benzenoid
Pyrrolidine
Cyclic carboximidic acid
Cyclic alcohol
Tertiary carboxylic acid amide
Carboxamide group
Secondary alcohol
Lactam
Carboxylic acid derivative
Ether
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
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	2.67	ChemAxon
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	0.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.95 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	125.9 m³·mol⁻¹	ChemAxon
Polarizability	49.56 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

78155618

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-8'-one (NP0302638)

MOL for NP0302638 (2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-8'-one)

3D MOL for NP0302638 (2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-8'-one)

3D SDF for NP0302638 (2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-8'-one)

3D-SDF for NP0302638 (2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-8'-one)

PDB for NP0302638 (2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-8'-one)

3D PDB for NP0302638 (2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-8'-one)

SMILES for NP0302638 (2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-8'-one)

INCHI for NP0302638 (2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-8'-one)

Structure for NP0302638 (2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-8'-one)

3D Structure for NP0302638 (2,6',13'-trihydroxy-4',4',7,7-tetramethyl-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-en-8'-one)