NP-MRD: Showing NP-Card for 10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione (NP0199140)

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Record Information

Version

2.0

Created at

2022-09-04 17:43:15 UTC

Updated at

2022-09-04 17:43:15 UTC

NP-MRD ID

NP0199140

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione

Description

10A-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione 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. 10A-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241501512D          

 33 36  0  0  0  0            999 V2000
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    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004241501512D          

 33 36  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0199140

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2(CC3C(=C)CCC(Br)C3(C)C)C(=O)C3=CC(O)=CC(O)=C3C(=O)C2(Cl)CC1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C25H29BrCl2O5/c1-12-6-7-17(26)22(2,3)15(12)10-25-20(31)14-8-13(29)9-16(30)19(14)21(32)24(25,28)11-18(27)23(4,5)33-25/h8-9,15,17-18,29-30H,1,6-7,10-11H2,2-5H3

> <INCHI_KEY>
PVEFIGXLPBGZAX-UHFFFAOYSA-N

> <FORMULA>
C25H29BrCl2O5

> <MOLECULAR_WEIGHT>
560.31

> <EXACT_MASS>
558.057542

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
52.13179063403431

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione

> <ALOGPS_LOGP>
5.64

> <JCHEM_LOGP>
6.525393131666666

> <ALOGPS_LOGS>
-6.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.835394596229213

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.19929088183905

> <JCHEM_PKA_STRONGEST_BASIC>
-4.287282773277508

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
131.77269999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.85e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3H,4H-naphtho[2,3-b]pyran-5,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.151  -3.347   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.141  -1.633   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -1.540   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  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   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   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0       0.000  -1.540   0.000  0.00  0.00          Br+0
HETATM   14  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.390  -2.900   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.944  -2.900   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   30 Cl   UNK     0       5.335  -6.160   0.000  0.00  0.00          Cl+0
HETATM   31  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   33 Cl   UNK     0       1.334  -5.390   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    4   32                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   17   29                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15   16                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    5   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    5   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    2   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₉BrCl₂O₅

Average Mass

560.3100 Da

Monoisotopic Mass

558.05754 Da

IUPAC Name

10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione

Traditional Name

10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3H,4H-naphtho[2,3-b]pyran-5,10-dione

CAS Registry Number

Not Available

SMILES

CC1(C)OC2(CC3C(=C)CCC(Br)C3(C)C)C(=O)C3=CC(O)=CC(O)=C3C(=O)C2(Cl)CC1Cl

InChI Identifier

InChI=1S/C25H29BrCl2O5/c1-12-6-7-17(26)22(2,3)15(12)10-25-20(31)14-8-13(29)9-16(30)19(14)21(32)24(25,28)11-18(27)23(4,5)33-25/h8-9,15,17-18,29-30H,1,6-7,10-11H2,2-5H3

InChI Key

PVEFIGXLPBGZAX-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

Not Available

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
Naphthoquinone
Naphthalene
Tetralin
Quinone
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Oxane
Vinylogous acid
Alpha-haloketone
Alpha-chloroketone
Ketone
Oxacycle
Dialkyl ether
Ether
Organic oxygen compound
Organohalogen compound
Alkyl bromide
Organobromide
Organochloride
Organooxygen compound
Alkyl chloride
Alkyl halide
Organic oxide
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	5.64	ALOGPS
logP	6.53	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	7.2	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	131.77 m³·mol⁻¹	ChemAxon
Polarizability	52.13 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

13787856

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione (NP0199140)

MOL for NP0199140 (10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D MOL for NP0199140 (10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D SDF for NP0199140 (10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D-SDF for NP0199140 (10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

PDB for NP0199140 (10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D PDB for NP0199140 (10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

SMILES for NP0199140 (10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

INCHI for NP0199140 (10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

Structure for NP0199140 (10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D Structure for NP0199140 (10a-[(3-bromo-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)