NP-MRD: Showing NP-Card for 3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione (NP0255247)

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Record Information

Version

1.0

Created at

2022-09-07 19:40:22 UTC

Updated at

2022-09-07 19:40:22 UTC

NP-MRD ID

NP0255247

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione

Description

3,4A-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-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-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione is found in Streptomyces aculeolatus. Based on a literature review very few articles have been published on 3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-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


  Mrv1652309072221402D          

 37 40  0  0  0  0            999 V2000
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  CHG  2  34   1  35  -1
M  END

     RDKit          3D

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M  CHG  2  34   1  35  -1
M  END


  Mrv1652309072221402D          

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  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
  9 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  2  0  0  0  0
  6 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  2  0  0  0  0
 33 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  CHG  2  34   1  35  -1
M  END
> <DATABASE_ID>
NP0255247

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C2=C(C(=O)C3(CC4C(C)(O)CCC(Cl)C4(C)C)OC(C)(C)C(Cl)CC3(Cl)C2=O)C(=[N+]=[N-])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H31Cl3N2O6/c1-11-18(32)16-15(17(31-30)19(11)33)21(35)26(9-12-22(2,3)13(27)7-8-24(12,6)36)25(29,20(16)34)10-14(28)23(4,5)37-26/h12-14,32,36H,7-10H2,1-6H3

> <INCHI_KEY>
DTXSUAICQAUGGW-UHFFFAOYSA-N

> <FORMULA>
C26H31Cl3N2O6

> <MOLECULAR_WEIGHT>
573.89

> <EXACT_MASS>
572.1247698

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.95210020739762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-9-(-lambda5-diazynylidene)-2,2,7-trimethyl-2H,3H,4H,4aH,5H,8H,9H,10H,10aH-naphtho[2,3-b]pyran-5,8,10-trione

> <JCHEM_LOGP>
3.4673294541240542

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.918646023463738

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2665309914746525

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9023984249988493

> <JCHEM_POLAR_SURFACE_AREA>
117.97

> <JCHEM_REFRACTIVITY>
139.17249999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-9-(-lambda5-diazynylidene)-2,2,7-trimethyl-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       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.850  -3.583   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.860  -5.297   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0      -2.667  -1.540   0.000  0.00  0.00          Cl+0
HETATM   19  C   UNK     0      -0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.723  -0.180   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.723  -0.180   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.527  -1.447   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.517   0.267   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   27 Cl   UNK     0      -1.334   2.310   0.000  0.00  0.00          Cl+0
HETATM   28  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   30 Cl   UNK     0       2.667   3.080   0.000  0.00  0.00          Cl+0
HETATM   31  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+1
HETATM   35  N   UNK     0       6.668  -3.850   0.000  0.00  0.00           N-1
HETATM   36  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   31                                                  
CONECT    6    5    7   33                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   22   29                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11   20   21                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    9   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28    9   30   31                                             
CONECT   30   29                                                            
CONECT   31   29    5   32                                                  
CONECT   32   31                                                            
CONECT   33    6   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33    2   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₁Cl₃N₂O₆

Average Mass

573.8900 Da

Monoisotopic Mass

572.12477 Da

IUPAC Name

3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-9-(-lambda5-diazynylidene)-2,2,7-trimethyl-2H,3H,4H,4aH,5H,8H,9H,10H,10aH-naphtho[2,3-b]pyran-5,8,10-trione

Traditional Name

3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-9-(-lambda5-diazynylidene)-2,2,7-trimethyl-3H,4H-naphtho[2,3-b]pyran-5,8,10-trione

CAS Registry Number

Not Available

SMILES

CC1=C(O)C2=C(C(=O)C3(CC4C(C)(O)CCC(Cl)C4(C)C)OC(C)(C)C(Cl)CC3(Cl)C2=O)C(=[N+]=[N-])C1=O

InChI Identifier

InChI=1S/C26H31Cl3N2O6/c1-11-18(32)16-15(17(31-30)19(11)33)21(35)26(9-12-22(2,3)13(27)7-8-24(12,6)36)25(29,20(16)34)10-14(28)23(4,5)37-26/h12-14,32,36H,7-10H2,1-6H3

InChI Key

DTXSUAICQAUGGW-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 aculeolatus	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
Cyclohexyl halide
Cyclohexenone
Pyranone
Cyclohexanol
Pyran
Oxane
Alpha-haloketone
Alpha-chloroketone
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
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
Alcohol
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
logP	3.47	ChemAxon
pKa (Strongest Acidic)	2.27	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	117.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	139.17 m³·mol⁻¹	ChemAxon
Polarizability	55.95 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

163188737

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-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione (NP0255247)

MOL for NP0255247 (3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

3D MOL for NP0255247 (3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

3D SDF for NP0255247 (3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

3D-SDF for NP0255247 (3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

PDB for NP0255247 (3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

3D PDB for NP0255247 (3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

SMILES for NP0255247 (3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

INCHI for NP0255247 (3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

Structure for NP0255247 (3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)

3D Structure for NP0255247 (3,4a-dichloro-10a-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-6-hydroxy-2,2,7-trimethyl-9-(λ⁵-diazynylidene)-3h,4h-naphtho[2,3-b]pyran-5,8,10-trione)