NP-MRD: Showing NP-Card for (3r,10ar)-3-chloro-10a-{[(3s,6s)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione (NP0195038)

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Record Information

Version

2.0

Created at

2022-09-04 12:49:03 UTC

Updated at

2022-09-04 12:49:04 UTC

NP-MRD ID

NP0195038

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,10ar)-3-chloro-10a-{[(3s,6s)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione

Description

(3R,10aR)-3-chloro-10a-{[(3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-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. Based on a literature review very few articles have been published on (3R,10aR)-3-chloro-10a-{[(3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042214492D          

 35 38  0  0  1  0            999 V2000
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M  END

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  Mrv1652309042214492D          

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 24 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  1  0  0  0
 21 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0195038

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C=C2C(=O)[C@]3(CC4[C@@](C)(O)CC[C@H](Cl)C4(C)C)OC(C)(C)[C@H](Cl)CC3(O)C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34Cl2O7/c1-12-14(29)9-13-18(19(12)30)21(32)25(34)11-17(28)23(4,5)35-26(25,20(13)31)10-15-22(2,3)16(27)7-8-24(15,6)33/h9,15-17,29-30,33-34H,7-8,10-11H2,1-6H3/t15?,16-,17+,24-,25?,26-/m0/s1

> <INCHI_KEY>
NLLBVEYNGJBFKB-ZFARLDKKSA-N

> <FORMULA>
C26H34Cl2O7

> <MOLECULAR_WEIGHT>
529.45

> <EXACT_MASS>
528.1681588

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.34582472929354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,10aR)-3-chloro-10a-{[(3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione

> <JCHEM_LOGP>
4.531165988333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.143157707027639

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.607045952758184

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9024267896327656

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
132.684

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,10aR)-3-chloro-10a-{[(3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3H,4H-naphtho[2,3-b]pyran-5,10-dione

> <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       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.668   2.310   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0      -1.334  -0.770   0.000  0.00  0.00          Cl+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.527   2.987   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.517   1.273   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.850   5.123   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.860   6.837   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.000   6.160   0.000  0.00  0.00           C+0
HETATM   28 Cl   UNK     0      -0.000   7.700   0.000  0.00  0.00          Cl+0
HETATM   29  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.723   1.720   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.723   1.720   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   21                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   12   22   34                                             
CONECT   22   21   23                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   23   32   33                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   21    6   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

C₂₆H₃₄Cl₂O₇

Average Mass

529.4500 Da

Monoisotopic Mass

528.16816 Da

IUPAC Name

(3R,10aR)-3-chloro-10a-{[(3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione

Traditional Name

(3R,10aR)-3-chloro-10a-{[(3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3H,4H-naphtho[2,3-b]pyran-5,10-dione

CAS Registry Number

Not Available

SMILES

CC1=C(O)C=C2C(=O)[C@]3(CC4[C@@](C)(O)CC[C@H](Cl)C4(C)C)OC(C)(C)[C@H](Cl)CC3(O)C(=O)C2=C1O

InChI Identifier

InChI=1S/C26H34Cl2O7/c1-12-14(29)9-13-18(19(12)30)21(32)25(34)11-17(28)23(4,5)35-26(25,20(13)31)10-15-22(2,3)16(27)7-8-24(15,6)33/h9,15-17,29-30,33-34H,7-8,10-11H2,1-6H3/t15?,16-,17+,24-,25?,26-/m0/s1

InChI Key

NLLBVEYNGJBFKB-ZFARLDKKSA-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
Tetralin
Naphthalene
Aryl alkyl ketone
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexyl halide
Pyranone
Cyclohexanol
Benzenoid
Pyran
Oxane
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Ketone
Oxacycle
Polyol
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
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	4.53	ChemAxon
pKa (Strongest Acidic)	7.61	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	132.68 m³·mol⁻¹	ChemAxon
Polarizability	53.35 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

145720575

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,10ar)-3-chloro-10a-{[(3s,6s)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione (NP0195038)

MOL for NP0195038 ((3r,10ar)-3-chloro-10a-{[(3s,6s)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D MOL for NP0195038 ((3r,10ar)-3-chloro-10a-{[(3s,6s)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D SDF for NP0195038 ((3r,10ar)-3-chloro-10a-{[(3s,6s)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D-SDF for NP0195038 ((3r,10ar)-3-chloro-10a-{[(3s,6s)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

PDB for NP0195038 ((3r,10ar)-3-chloro-10a-{[(3s,6s)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D PDB for NP0195038 ((3r,10ar)-3-chloro-10a-{[(3s,6s)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

SMILES for NP0195038 ((3r,10ar)-3-chloro-10a-{[(3s,6s)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

INCHI for NP0195038 ((3r,10ar)-3-chloro-10a-{[(3s,6s)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

Structure for NP0195038 ((3r,10ar)-3-chloro-10a-{[(3s,6s)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D Structure for NP0195038 ((3r,10ar)-3-chloro-10a-{[(3s,6s)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-4a,6,8-trihydroxy-2,2,7-trimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)