NP-MRD: Showing NP-Card for 3,4a-dichloro-10a-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione (NP0191140)

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Record Information

Version

2.0

Created at

2022-09-04 07:59:17 UTC

Updated at

2022-09-04 07:59:17 UTC

NP-MRD ID

NP0191140

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

3,4A-dichloro-10a-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-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 vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position. 3,4a-dichloro-10a-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione is found in Streptomyces antimycoticus. 3,4A-dichloro-10a-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-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


  Mrv1533004191518322D          

 33 35  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145    2.8875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004191518322D          

 33 35  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0191140

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H28Cl2O6/c1-13(2)17(29)7-6-14(3)8-9-25-21(31)16-10-15(28)11-18(30)20(16)22(32)24(25,27)12-19(26)23(4,5)33-25/h8,10-11,19,28,30H,1,6-7,9,12H2,2-5H3

> <INCHI_KEY>
YAMAETJPGJWVHQ-UHFFFAOYSA-N

> <FORMULA>
C25H28Cl2O6

> <MOLECULAR_WEIGHT>
495.39

> <EXACT_MASS>
494.126294

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
50.52068311775645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.35

> <JCHEM_LOGP>
5.909051253666667

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.834839826507254

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.198705365859053

> <JCHEM_PKA_STRONGEST_BASIC>
-4.144795270764953

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
127.74639999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.22e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.657   0.360   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.677   0.360   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       0.000   1.540   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       1.334   5.390   0.000  0.00  0.00          Cl+0
HETATM   15  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002   9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13   25                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   24                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   17   25                                                  
CONECT   25   24    5   26                                                  
CONECT   26   25                                                            
CONECT   27    2   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈Cl₂O₆

Average Mass

495.3900 Da

Monoisotopic Mass

494.12629 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(CCC(=O)C(C)=C)=CCC12OC(C)(C)C(Cl)CC1(Cl)C(=O)C1=C(O)C=C(O)C=C1C2=O

InChI Identifier

InChI=1S/C25H28Cl2O6/c1-13(2)17(29)7-6-14(3)8-9-25-21(31)16-10-15(28)11-18(30)20(16)22(32)24(25,27)12-19(26)23(4,5)33-25/h8,10-11,19,28,30H,1,6-7,9,12H2,2-5H3

InChI Key

YAMAETJPGJWVHQ-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 vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Vitamin K compounds

Alternative Parents

Substituents

Naphthopyranone
Naphthopyran
Naphthoquinone
Aromatic monoterpenoid
Monoterpenoid
Naphthalene
Tetralin
Quinone
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Oxane
Pyran
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Vinylogous acid
Acryloyl-group
Alpha,beta-unsaturated ketone
Alpha-haloketone
Enone
Alpha-chloroketone
Ketone
Organoheterocyclic compound
Dialkyl ether
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organohalogen compound
Carbonyl group
Organochloride
Alkyl chloride
Alkyl halide
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	4.35	ALOGPS
logP	5.91	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	7.2	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	127.75 m³·mol⁻¹	ChemAxon
Polarizability	50.52 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

74336643

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-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione (NP0191140)

MOL for NP0191140 (3,4a-dichloro-10a-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D MOL for NP0191140 (3,4a-dichloro-10a-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D SDF for NP0191140 (3,4a-dichloro-10a-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D-SDF for NP0191140 (3,4a-dichloro-10a-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

PDB for NP0191140 (3,4a-dichloro-10a-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D PDB for NP0191140 (3,4a-dichloro-10a-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

SMILES for NP0191140 (3,4a-dichloro-10a-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

INCHI for NP0191140 (3,4a-dichloro-10a-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

Structure for NP0191140 (3,4a-dichloro-10a-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D Structure for NP0191140 (3,4a-dichloro-10a-(3,7-dimethyl-6-oxoocta-2,7-dien-1-yl)-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)