NP-MRD: Showing NP-Card for 3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione (NP0241669)

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Record Information

Version

2.0

Created at

2022-09-07 01:48:26 UTC

Updated at

2022-09-07 01:48:26 UTC

NP-MRD ID

NP0241669

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione

Description

3,4A-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-2H,3H,4H,4aH,5H,8H,9H,10H,10aH-naphtho[2,3-b]pyran-5,8,10-trione belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. 3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione is found in Streptomyces antimycoticus. Based on a literature review very few articles have been published on 3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-2H,3H,4H,4aH,5H,8H,9H,10H,10aH-naphtho[2,3-b]pyran-5,8,10-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072203482D          

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M  CHG  2  29   1  30  -1
M  END

     RDKit          3D

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M  CHG  2  29   1  30  -1
M  END


  Mrv1652309072203482D          

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M  CHG  2  29   1  30  -1
M  END
> <DATABASE_ID>
NP0241669

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2(CC3C(=C)CCC(Cl)C3(C)C)C(=O)C3=C(C(O)=CC(=O)C3=[N+]=[N-])C(=O)C2(Cl)CC1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C25H27Cl3N2O5/c1-11-6-7-15(26)22(2,3)12(11)9-25-21(34)18-17(13(31)8-14(32)19(18)30-29)20(33)24(25,28)10-16(27)23(4,5)35-25/h8,12,15-16,31H,1,6-7,9-10H2,2-5H3

> <INCHI_KEY>
HYDZZTKLIACTQZ-UHFFFAOYSA-N

> <FORMULA>
C25H27Cl3N2O5

> <MOLECULAR_WEIGHT>
541.85

> <EXACT_MASS>
540.0985551

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
52.40119652609695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-9-(-lambda5-diazynylidene)-2,2-dimethyl-2H,3H,4H,4aH,5H,8H,9H,10H,10aH-naphtho[2,3-b]pyran-5,8,10-trione

> <JCHEM_LOGP>
4.039340378790721

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.921136517516892

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.3861029135056007

> <JCHEM_PKA_STRONGEST_BASIC>
-4.287429399017288

> <JCHEM_POLAR_SURFACE_AREA>
97.74000000000001

> <JCHEM_REFRACTIVITY>
132.91079999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-9-(-lambda5-diazynylidene)-2,2-dimethyl-3H,4H-naphtho[2,3-b]pyran-5,8,10-trione

> <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  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0      10.669  -1.540   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.992  -0.360   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.012  -0.360   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.529  -1.447   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.519   0.267   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       9.336   2.310   0.000  0.00  0.00          Cl+0
HETATM   19  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       5.335   3.080   0.000  0.00  0.00          Cl+0
HETATM   22  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+1
HETATM   30  N   UNK     0       1.334  -3.850   0.000  0.00  0.00           N-1
HETATM   31  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20   26                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   12   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   34                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   12   27                                                  
CONECT   27   26                                                            
CONECT   28   25   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   24   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₇Cl₃N₂O₅

Average Mass

541.8500 Da

Monoisotopic Mass

540.09856 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)OC2(CC3C(=C)CCC(Cl)C3(C)C)C(=O)C3=C(C(O)=CC(=O)C3=[N+]=[N-])C(=O)C2(Cl)CC1Cl

InChI Identifier

InChI=1S/C25H27Cl3N2O5/c1-11-6-7-15(26)22(2,3)12(11)9-25-21(34)18-17(13(31)8-14(32)19(18)30-29)20(33)24(25,28)10-16(27)23(4,5)35-25/h8,12,15-16,31H,1,6-7,9-10H2,2-5H3

InChI Key

HYDZZTKLIACTQZ-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
Streptomyces antimycoticus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Naphthalene
Cyclohexenone
Pyranone
Pyran
Oxane
Alpha-haloketone
Alpha-chloroketone
Vinylogous acid
Cyclic ketone
Ketone
Oxacycle
Ether
Enol
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

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

163189299

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione (NP0241669)

MOL for NP0241669 (3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

3D MOL for NP0241669 (3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

3D SDF for NP0241669 (3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

3D-SDF for NP0241669 (3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

PDB for NP0241669 (3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

3D PDB for NP0241669 (3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

SMILES for NP0241669 (3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

INCHI for NP0241669 (3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

Structure for NP0241669 (3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

3D Structure for NP0241669 (3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6-hydroxy-2,2-dimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)