NP-MRD: Showing NP-Card for (3r,4ar,10as)-3,4a-dichloro-10a-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione (NP0235939)

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Record Information

Version

2.0

Created at

2022-09-06 18:42:46 UTC

Updated at

2022-09-06 18:42:46 UTC

NP-MRD ID

NP0235939

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Napyradiomycin A1, also known as NPD-a1 or WS 9558 a, 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. (3r,4ar,10as)-3,4a-dichloro-10a-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione is found in Streptomyces aculeolatus, Streptomyces antimycoticus and Streptomyces ruber. (3r,4ar,10as)-3,4a-dichloro-10a-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione was first documented in 2009 (PMID: 19338329). Based on a literature review a small amount of articles have been published on Napyradiomycin A1 (PMID: 23771045) (PMID: 27763545) (PMID: 28749137) (PMID: 22252199).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062220422D          

 32 34  0  0  1  0            999 V2000
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -1.2375    0.0000 O   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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   -4.3201   -2.1409   -1.0728 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3515   -1.9395    0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3662   -0.4464    0.8882 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6008   -0.0422    2.4904 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7586    0.0174    1.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6477   -0.7855    1.3686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0968    1.4143    0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0642    2.0446    1.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3236    3.4011    1.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6095    4.0601    0.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3403    0.7369   -1.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1895   -1.4061   -3.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
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 29 62  1  0
M  END


  Mrv1652309062220422D          

 32 34  0  0  1  0            999 V2000
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    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>
NP0235939

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\C[C@@]12OC(C)(C)[C@H](Cl)C[C@]1(Cl)C(=O)C1=C(O)C=C(O)C=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30Cl2O5/c1-14(2)7-6-8-15(3)9-10-25-21(30)17-11-16(28)12-18(29)20(17)22(31)24(25,27)13-19(26)23(4,5)32-25/h7,9,11-12,19,28-29H,6,8,10,13H2,1-5H3/b15-9+/t19-,24+,25+/m1/s1

> <INCHI_KEY>
BCPWMPCOEAOEDD-NQSCOFRMSA-N

> <FORMULA>
C25H30Cl2O5

> <MOLECULAR_WEIGHT>
481.41

> <EXACT_MASS>
480.1470295

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
49.70259868763047

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
6.518400944666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.834839826507388

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.19870536585867

> <JCHEM_PKA_STRONGEST_BASIC>
-4.289350667760219

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
128.12569999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4aR,10aS)-3,4a-dichloro-10a-[(2E)-3,7-dimethylocta-2,6-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                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.529   2.987   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.519   1.273   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       9.336  -0.770   0.000  0.00  0.00          Cl+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0       5.335  -1.540   0.000  0.00  0.00          Cl+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+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
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19   31                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   11   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   30                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   23   31                                                  
CONECT   31   30   11   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
NPD-a1	MeSH
WS 9558 a	MeSH
Napyrodiomycin a	MeSH

Chemical Formula

C₂₅H₃₀Cl₂O₅

Average Mass

481.4100 Da

Monoisotopic Mass

480.14703 Da

IUPAC Name

(3R,4aR,10aS)-3,4a-dichloro-10a-[(2E)-3,7-dimethylocta-2,6-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

(3R,4aR,10aS)-3,4a-dichloro-10a-[(2E)-3,7-dimethylocta-2,6-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(C)=CCC\C(C)=C\C[C@@]12OC(C)(C)[C@H](Cl)C[C@]1(Cl)C(=O)C1=C(O)C=C(O)C=C1C2=O

InChI Identifier

InChI=1S/C25H30Cl2O5/c1-14(2)7-6-8-15(3)9-10-25-21(30)17-11-16(28)12-18(29)20(17)22(31)24(25,27)13-19(26)23(4,5)32-25/h7,9,11-12,19,28-29H,6,8,10,13H2,1-5H3/b15-9+/t19-,24+,25+/m1/s1

InChI Key

BCPWMPCOEAOEDD-NQSCOFRMSA-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
Streptomyces antimycoticus	LOTUS Database	35616633
Streptomyces ruber	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
Aromatic monoterpenoid
Monoterpenoid
Naphthalene
Tetralin
Aryl alkyl ketone
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Oxane
Pyran
Benzenoid
Vinylogous acid
Alpha-haloketone
Alpha-chloroketone
Ketone
Dialkyl ether
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Alkyl halide
Organohalogen compound
Organochloride
Organooxygen compound
Alkyl chloride
Hydrocarbon derivative
Organic oxide
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	6.52	ChemAxon
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	5	ChemAxon
Refractivity	128.13 m³·mol⁻¹	ChemAxon
Polarizability	49.7 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00038179

Chemspider ID

4943391

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6438953

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wu Z, Li S, Li J, Chen Y, Saurav K, Zhang Q, Zhang H, Zhang W, Zhang W, Zhang S, Zhang C: Antibacterial and cytotoxic new napyradiomycins from the marine-derived Streptomyces sp. SCSIO 10428. Mar Drugs. 2013 Jun 14;11(6):2113-25. doi: 10.3390/md11062113. [PubMed:23771045 ]
Lacret R, Perez-Victoria I, Oves-Costales D, de la Cruz M, Domingo E, Martin J, Diaz C, Vicente F, Genilloud O, Reyes F: MDN-0170, a New Napyradiomycin from Streptomyces sp. Strain CA-271078. Mar Drugs. 2016 Oct 18;14(10). pii: md14100188. doi: 10.3390/md14100188. [PubMed:27763545 ]
Hwang JS, Kim GJ, Choi HG, Kim MC, Hahn D, Nam JW, Nam SJ, Kwon HC, Chin J, Cho SJ, Hwang H, Choi H: Identification of Antiangiogenic Potential and Cellular Mechanisms of Napyradiomycin A1 Isolated from the Marine-Derived Streptomyces sp. YP127. J Nat Prod. 2017 Aug 25;80(8):2269-2275. doi: 10.1021/acs.jnatprod.7b00211. Epub 2017 Jul 27. [PubMed:28749137 ]
Yamamoto K, Tashiro E, Motohashi K, Seto H, Imoto M: Napyradiomycin A1, an inhibitor of mitochondrial complexes I and II. J Antibiot (Tokyo). 2012 Apr;65(4):211-4. doi: 10.1038/ja.2011.138. Epub 2012 Jan 18. [PubMed:22252199 ]
Snyder SA, Tang ZY, Gupta R: Enantioselective total synthesis of (-)-napyradiomycin A1 via asymmetric chlorination of an isolated olefin. J Am Chem Soc. 2009 Apr 29;131(16):5744-5. doi: 10.1021/ja9014716. [PubMed:19338329 ]
LOTUS database [Link]

Showing NP-Card for (3r,4ar,10as)-3,4a-dichloro-10a-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione (NP0235939)

MOL for NP0235939 ((3r,4ar,10as)-3,4a-dichloro-10a-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D MOL for NP0235939 ((3r,4ar,10as)-3,4a-dichloro-10a-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D SDF for NP0235939 ((3r,4ar,10as)-3,4a-dichloro-10a-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D-SDF for NP0235939 ((3r,4ar,10as)-3,4a-dichloro-10a-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

PDB for NP0235939 ((3r,4ar,10as)-3,4a-dichloro-10a-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D PDB for NP0235939 ((3r,4ar,10as)-3,4a-dichloro-10a-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

SMILES for NP0235939 ((3r,4ar,10as)-3,4a-dichloro-10a-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

INCHI for NP0235939 ((3r,4ar,10as)-3,4a-dichloro-10a-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

Structure for NP0235939 ((3r,4ar,10as)-3,4a-dichloro-10a-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D Structure for NP0235939 ((3r,4ar,10as)-3,4a-dichloro-10a-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)