NP-MRD: Showing NP-Card for 11-o-acetylalkannin (NP0248448)

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Record Information

Version

2.0

Created at

2022-09-07 10:43:05 UTC

Updated at

2022-09-07 10:43:05 UTC

NP-MRD ID

NP0248448

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-o-acetylalkannin

Description

Acetylalkannin, also known as acetylshikonin, belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 11-o-acetylalkannin is found in Alkanna cappadocica, Arnebia decumbens, Arnebia euchroma and Arnebia hispidissima. Based on a literature review very few articles have been published on Acetylalkannin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -2.1737    3.4514   -2.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727    2.5240   -1.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3358    2.8070    0.0807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1189    1.3751   -1.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8840    0.5581   -0.0986 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4703   -0.8234   -0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9432   -0.7980   -0.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8000   -1.3786    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2540   -1.2700    0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3621   -2.1306    1.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5581    0.4321    0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637    0.9119    1.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4692    0.8201    1.7383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141    1.3199    2.8307 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4169    0.1681    0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7430    0.0755    1.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2514    0.5735    2.3766 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6111   -0.5702    0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1372   -1.0848   -0.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8047   -0.9780   -1.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3331   -1.5045   -2.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9194   -0.3480   -0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5032   -0.2299   -0.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1470   -0.7297   -1.7510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2651    3.4854   -2.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719    3.2624   -3.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9027    4.4791   -1.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3906    1.0077    0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9755   -1.3755   -1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2515   -1.3935    0.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292   -0.2696   -1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3964   -1.3854   -0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8029   -2.1056    0.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5870   -0.2770    0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2313   -2.2843    2.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6516   -1.4687    2.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9226   -3.1102    1.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3916    1.4090    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9267    1.0483    3.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6394   -0.6312    0.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8394   -1.5856   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239   -1.9765   -3.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
  8  7  2  3
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 23 11  1  0
 22 15  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
  7 31  1  0
  6 29  1  0
  6 30  1  0
  5 28  1  1
  1 25  1  0
  1 26  1  0
  1 27  1  0
 12 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 21 42  1  0
M  END


  Mrv1652309072212432D          

 24 25  0  0  1  0            999 V2000
    2.1434   -3.7125    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   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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
    5.0013   -3.7125    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   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   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
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0248448

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC[C@H](OC(C)=O)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c1-9(2)4-7-15(24-10(3)19)11-8-14(22)16-12(20)5-6-13(21)17(16)18(11)23/h4-6,8,15,20-21H,7H2,1-3H3/t15-/m0/s1

> <INCHI_KEY>
WNFXUXZJJKTDOZ-HNNXBMFYSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.336

> <EXACT_MASS>
330.1103383

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.0926180309323

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate

> <JCHEM_LOGP>
3.452766415

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.160527580988784

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.489934621321973

> <JCHEM_PKA_STRONGEST_BASIC>
-5.5649466977272555

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
88.97169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
11-O-acetylalkannin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.336  -2.310   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   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   22                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22   11   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
(1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-penten-1-yl acetate	MeSH
Acetylshikonin	MeSH
Acetylshikonin, (+-)-isomer	MeSH
Acetylshikonin, (R)-isomer	MeSH
Acetylshikonin, (S)-isomer	MeSH

Chemical Formula

C₁₈H₁₈O₆

Average Mass

330.3360 Da

Monoisotopic Mass

330.11034 Da

IUPAC Name

(1S)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate

Traditional Name

11-O-acetylalkannin

CAS Registry Number

Not Available

SMILES

CC(C)=CC[C@H](OC(C)=O)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C18H18O6/c1-9(2)4-7-15(24-10(3)19)11-8-14(22)16-12(20)5-6-13(21)17(16)18(11)23/h4-6,8,15,20-21H,7H2,1-3H3/t15-/m0/s1

InChI Key

WNFXUXZJJKTDOZ-HNNXBMFYSA-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
Alkanna cappadocica	LOTUS Database	35616633
Arnebia decumbens	LOTUS Database	35616633
Arnebia euchroma	LOTUS Database	35616633
Arnebia hispidissima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Aromatic monoterpenoid
Bicyclic monoterpenoid
Monoterpenoid
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.45	ChemAxon
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	88.97 m³·mol⁻¹	ChemAxon
Polarizability	33.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

8142877

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9967285

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 11-o-acetylalkannin (NP0248448)

MOL for NP0248448 (11-o-acetylalkannin)

3D MOL for NP0248448 (11-o-acetylalkannin)

3D SDF for NP0248448 (11-o-acetylalkannin)

3D-SDF for NP0248448 (11-o-acetylalkannin)

PDB for NP0248448 (11-o-acetylalkannin)

3D PDB for NP0248448 (11-o-acetylalkannin)

SMILES for NP0248448 (11-o-acetylalkannin)

INCHI for NP0248448 (11-o-acetylalkannin)

Structure for NP0248448 (11-o-acetylalkannin)

3D Structure for NP0248448 (11-o-acetylalkannin)