NP-MRD: Showing NP-Card for 3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione (NP0242905)

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Record Information

Version

2.0

Created at

2022-09-07 03:20:10 UTC

Updated at

2022-09-07 03:20:10 UTC

NP-MRD ID

NP0242905

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione

Description

3,4A-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-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 menaquinones. These are vitamin K2 compounds consisting of a naphtho-1,4-quinone ring system, which is substituted at the 2-position by an isoprenyl side-chain, and usually, at the 3-position by a methyl group. 3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione is found in Streptomyces antimycoticus. 3,4A-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-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


  Mrv1533004241500022D          

 33 35  0  0  0  0            999 V2000
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    3.5724    2.0625    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


  Mrv1533004241500022D          

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M  END
> <DATABASE_ID>
NP0242905

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CO)=CCCC(C)=CCC12OC(C)(C)C(Cl)CC1(Cl)C(=O)C1=C(O)C=C(O)C=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30Cl2O6/c1-14(6-5-7-15(2)13-28)8-9-25-21(31)17-10-16(29)11-18(30)20(17)22(32)24(25,27)12-19(26)23(3,4)33-25/h7-8,10-11,19,28-30H,5-6,9,12-13H2,1-4H3

> <INCHI_KEY>
ADDJEJWGIYLORW-UHFFFAOYSA-N

> <FORMULA>
C25H30Cl2O6

> <MOLECULAR_WEIGHT>
497.41

> <EXACT_MASS>
496.1419441

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.56124117705414

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione

> <ALOGPS_LOGP>
4.77

> <JCHEM_LOGP>
5.237629788000001

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.834839819923978

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.198705365702904

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0797068162575387

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
129.90039999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-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       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   3.080   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  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.529   2.987   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.519   1.273   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       9.336  -0.770   0.000  0.00  0.00          Cl+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       5.335  -1.540   0.000  0.00  0.00          Cl+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.334  10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17   29                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    9   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   21   29                                                  
CONECT   29   28    9   30                                                  
CONECT   30   29                                                            
CONECT   31    6                                                            
CONECT   32    2   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₀Cl₂O₆

Average Mass

497.4100 Da

Monoisotopic Mass

496.14194 Da

IUPAC Name

3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione

Traditional Name

3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3H,4H-naphtho[2,3-b]pyran-5,10-dione

CAS Registry Number

Not Available

SMILES

CC(CO)=CCCC(C)=CCC12OC(C)(C)C(Cl)CC1(Cl)C(=O)C1=C(O)C=C(O)C=C1C2=O

InChI Identifier

InChI=1S/C25H30Cl2O6/c1-14(6-5-7-15(2)13-28)8-9-25-21(31)17-10-16(29)11-18(30)20(17)22(32)24(25,27)12-19(26)23(3,4)33-25/h7-8,10-11,19,28-30H,5-6,9,12-13H2,1-4H3

InChI Key

ADDJEJWGIYLORW-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 menaquinones. These are vitamin K2 compounds consisting of a naphtho-1,4-quinone ring system, which is substituted at the 2-position by an isoprenyl side-chain, and usually, at the 3-position by a methyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Menaquinones

Alternative Parents

Substituents

Menaquinone
Naphthopyranone
Naphthopyran
Naphthoquinone
Tetralin
Naphthalene
Monoterpenoid
Aromatic monoterpenoid
Aryl alkyl ketone
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Pyranone
Oxane
Benzenoid
Pyran
Alpha-haloketone
Vinylogous acid
Alpha-chloroketone
Ketone
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Alkyl halide
Hydrocarbon derivative
Organic oxide
Alkyl chloride
Alcohol
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organohalogen compound
Organochloride
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	4.77	ALOGPS
logP	5.24	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	7.2	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	129.9 m³·mol⁻¹	ChemAxon
Polarizability	51.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

74336641

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-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione (NP0242905)

MOL for NP0242905 (3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D MOL for NP0242905 (3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D SDF for NP0242905 (3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D-SDF for NP0242905 (3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

PDB for NP0242905 (3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D PDB for NP0242905 (3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

SMILES for NP0242905 (3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

INCHI for NP0242905 (3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

Structure for NP0242905 (3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D Structure for NP0242905 (3,4a-dichloro-6,8-dihydroxy-10a-(8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)