NP-MRD: Showing NP-Card for beta-hydroxyisovalerylshikonin (NP0036680)

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Record Information

Version

2.0

Created at

2021-06-20 19:47:23 UTC

Updated at

2021-06-30 00:08:27 UTC

NP-MRD ID

NP0036680

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-hydroxyisovalerylshikonin

Provided By

JEOL Database JEOL Logo

Description

Beta-Hydroxyisovalerylshikonin, also known as beta-hivs, 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). beta-hydroxyisovalerylshikonin is found in Echium plantagineum, Lithospermum erythrorhizon and Onosma paniculata. beta-hydroxyisovalerylshikonin was first documented in 2013 (PMID: 23638460). Based on a literature review a significant number of articles have been published on beta-Hydroxyisovalerylshikonin (PMID: 33191109) (PMID: 33169745) (PMID: 32727911) (PMID: 32726058) (PMID: 32038116) (PMID: 28435429).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121473D          

 52 53  0  0  0  0            999 V2000
    0.1109    3.9872   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1271    3.3570   -0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5146    3.8976   -2.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637    2.3927   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6407    1.7361    1.1293 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1905    0.2570    1.0282 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2532   -0.5351    0.4419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2480   -0.9262    1.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3065   -0.6374    2.4722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2789   -1.7179    0.5204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1008   -2.7069    1.3585 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0646   -2.0199    2.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2186   -3.7187    2.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8968   -3.4726    0.4350 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0690    0.0893    0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095   -0.4484   -1.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3455   -1.0746   -2.9264 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -0.0471   -1.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7974   -0.1002   -1.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -0.6235   -3.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9780    0.3923   -1.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9689    0.9410   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7796    0.9934    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8613    1.5467    1.8552 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5854    0.5011    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3283    0.5612    0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3418    1.0010    1.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3987    3.5794    0.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7078    3.7276   -2.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9741    1.5038    2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  2  0  0  0  0
  4  2  2  3  0  0  0
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  2  1  1  0  0  0  0
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  2  3  1  0  0  0  0
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  6  7  1  0  0  0  0
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  7  8  1  0  0  0  0
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 22 20  1  0  0  0  0
 11 13  1  0  0  0  0
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 11 14  1  6  0  0  0
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  6 38  1  1  0  0  0
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  4 35  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
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 13 44  1  0  0  0  0
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 13 46  1  0  0  0  0
 14 47  1  0  0  0  0
M  END

     RDKit          3D

 52 53  0  0  0  0  0  0  0  0999 V2000
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   -6.0646   -2.0199    2.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1095   -0.4484   -1.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5973   -0.0471   -1.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8904   -0.6235   -3.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9689    0.9410   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7796    0.9934    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202121473D          

 52 53  0  0  0  0            999 V2000
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   -6.6919   -1.2901    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8312   -4.4967    2.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6079   -3.2517    2.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5524   -4.2348    1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6029   -2.8997    0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7816   -0.8102   -1.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0024   -0.9466   -3.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9038    0.3477   -1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8882    1.3263    0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9741    1.5038    2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  2  0  0  0  0
  4  2  2  3  0  0  0
 23 22  2  0  0  0  0
  2  1  1  0  0  0  0
 26 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 23  1  0  0  0  0
 20 21  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 19 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 16  1  0  0  0  0
  2  3  1  0  0  0  0
 16 15  2  0  0  0  0
  6  7  1  0  0  0  0
 15 27  1  0  0  0  0
  7  8  1  0  0  0  0
 26 19  1  0  0  0  0
  8 10  1  0  0  0  0
 15  6  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6  5  1  0  0  0  0
  8  9  2  0  0  0  0
 22 20  1  0  0  0  0
 11 13  1  0  0  0  0
  5  4  1  0  0  0  0
 11 14  1  6  0  0  0
 23 51  1  0  0  0  0
 22 50  1  0  0  0  0
 16 48  1  0  0  0  0
  6 38  1  1  0  0  0
  5 36  1  0  0  0  0
  5 37  1  0  0  0  0
  4 35  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 25 52  1  0  0  0  0
 21 49  1  0  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
 13 44  1  0  0  0  0
 13 45  1  0  0  0  0
 13 46  1  0  0  0  0
 14 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036680

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C([H])=C(C(=O)C2=C(O[H])C([H])=C1[H])[C@]([H])(OC(=O)C([H])([H])C(O[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O7/c1-11(2)5-8-16(28-17(25)10-21(3,4)27)12-9-15(24)18-13(22)6-7-14(23)19(18)20(12)26/h5-7,9,16,22-23,27H,8,10H2,1-4H3/t16-/m1/s1

> <INCHI_KEY>
MXANJRGHSFELEJ-MRXNPFEDSA-N

> <FORMULA>
C21H24O7

> <MOLECULAR_WEIGHT>
388.416

> <EXACT_MASS>
388.152203113

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
40.107676795609095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-hydroxy-3-methylbutanoate

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
3.569682798333334

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.160484988019611

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.489930898226968

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7421133083968394

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
104.43029999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-hydroxy-3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 53  0  0  0  0  0  0  0  0999 V2000
    0.1109    3.9872   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1271    3.3570   -0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5146    3.8976   -2.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637    2.3927   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6407    1.7361    1.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1905    0.2570    1.0282 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2532   -0.5351    0.4419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2480   -0.9262    1.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3065   -0.6374    2.4722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2789   -1.7179    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1008   -2.7069    1.3585 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0646   -2.0199    2.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2186   -3.7187    2.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8968   -3.4726    0.4350 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0690    0.0893    0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095   -0.4484   -1.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3522   -0.5649   -1.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3455   -1.0746   -2.9264 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -0.0471   -1.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7974   -0.1002   -1.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -0.6235   -3.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9780    0.3923   -1.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9689    0.9410   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7796    0.9934    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8613    1.5467    1.8552 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5854    0.5011    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3283    0.5612    0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3418    1.0010    1.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9583    3.8368   -0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    5.0640   -0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3987    3.5794    0.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7078    3.7276   -2.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4183    3.4219   -2.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7058    4.9738   -2.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7419    2.0212   -0.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283    2.3009    1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5944    1.7933    1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -0.1339    2.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9410   -1.0078    0.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7629   -2.2797   -0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5463   -1.5067    3.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7501   -2.7510    2.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6919   -1.2901    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8312   -4.4967    2.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6079   -3.2517    2.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5524   -4.2348    1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6029   -2.8997    0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7816   -0.8102   -1.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0024   -0.9466   -3.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9038    0.3477   -1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8882    1.3263    0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9741    1.5038    2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  2  0
  4  2  2  3
 23 22  2  0
  2  1  1  0
 26 24  2  0
 24 25  1  0
 24 23  1  0
 20 21  1  0
 26 27  1  0
 27 28  2  0
 19 17  1  0
 17 18  2  0
 17 16  1  0
  2  3  1  0
 16 15  2  0
  6  7  1  0
 15 27  1  0
  7  8  1  0
 26 19  1  0
  8 10  1  0
 15  6  1  0
 10 11  1  0
 11 12  1  0
  6  5  1  0
  8  9  2  0
 22 20  1  0
 11 13  1  0
  5  4  1  0
 11 14  1  6
 23 51  1  0
 22 50  1  0
 16 48  1  0
  6 38  1  1
  5 36  1  0
  5 37  1  0
  4 35  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 25 52  1  0
 21 49  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
 10 39  1  0
 10 40  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.111   3.987  -0.224  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.127   3.357  -0.801  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.515   3.898  -2.155  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.864   2.393  -0.215  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.641   1.736   1.129  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.190   0.257   1.028  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.253  -0.535   0.442  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.248  -0.926   1.288  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.307  -0.637   2.472  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.279  -1.718   0.520  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.101  -2.707   1.359  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.065  -2.020   2.329  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.219  -3.719   2.093  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.897  -3.473   0.435  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.069   0.089   0.196  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.110  -0.448  -1.032  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.352  -0.565  -1.811  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.345  -1.075  -2.926  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.597  -0.047  -1.225  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.797  -0.100  -1.949  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.890  -0.624  -3.211  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.978   0.392  -1.399  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.969   0.941  -0.118  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.780   0.993   0.606  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.861   1.547   1.855  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.585   0.501   0.057  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.328   0.561   0.828  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.342   1.001   1.974  0.00  0.00           O+0
HETATM   29  H   UNK     0       0.958   3.837  -0.901  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.041   5.064  -0.095  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.399   3.579   0.747  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.708   3.728  -2.875  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.418   3.422  -2.550  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.706   4.974  -2.092  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.742   2.021  -0.744  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.928   2.301   1.736  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.594   1.793   1.668  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.985  -0.134   2.034  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.941  -1.008   0.010  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.763  -2.280  -0.270  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.546  -1.507   3.143  0.00  0.00           H+0
HETATM   42  H   UNK     0      -6.750  -2.751   2.774  0.00  0.00           H+0
HETATM   43  H   UNK     0      -6.692  -1.290   1.805  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.831  -4.497   2.564  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.608  -3.252   2.871  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.552  -4.235   1.392  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.603  -2.900   0.089  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.782  -0.810  -1.534  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.002  -0.947  -3.485  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.904   0.348  -1.968  0.00  0.00           H+0
HETATM   51  H   UNK     0       5.888   1.326   0.317  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.974   1.504   2.278  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   32   33   34                                             
CONECT    4    2    5   35                                                  
CONECT    5    6    4   36   37                                             
CONECT    6    7   15    5   38                                             
CONECT    7    6    8                                                       
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   11   39   40                                             
CONECT   11   10   12   13   14                                             
CONECT   12   11   41   42   43                                             
CONECT   13   11   44   45   46                                             
CONECT   14   11   47                                                       
CONECT   15   16   27    6                                                  
CONECT   16   17   15   48                                                  
CONECT   17   19   18   16                                                  
CONECT   18   17                                                            
CONECT   19   20   17   26                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   49                                                       
CONECT   22   23   20   50                                                  
CONECT   23   22   24   51                                                  
CONECT   24   26   25   23                                                  
CONECT   25   24   52                                                       
CONECT   26   24   27   19                                                  
CONECT   27   26   28   15                                                  
CONECT   28   27                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    3                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   16                                                            
CONECT   49   21                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   25                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  106    0
END

RDKit          3D

52 53  0  0  0  0  0  0  0  0999 V2000
    0.1109    3.9872   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1271    3.3570   -0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5146    3.8976   -2.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637    2.3927   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6407    1.7361    1.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1905    0.2570    1.0282 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2532   -0.5351    0.4419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2480   -0.9262    1.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3065   -0.6374    2.4722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2789   -1.7179    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1008   -2.7069    1.3585 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0646   -2.0199    2.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2186   -3.7187    2.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8968   -3.4726    0.4350 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0690    0.0893    0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095   -0.4484   -1.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3522   -0.5649   -1.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3455   -1.0746   -2.9264 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -0.0471   -1.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7974   -0.1002   -1.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -0.6235   -3.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9780    0.3923   -1.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9689    0.9410   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7796    0.9934    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8613    1.5467    1.8552 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5854    0.5011    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3283    0.5612    0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3418    1.0010    1.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9583    3.8368   -0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    5.0640   -0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3987    3.5794    0.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7078    3.7276   -2.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4183    3.4219   -2.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7058    4.9738   -2.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7419    2.0212   -0.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283    2.3009    1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5944    1.7933    1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -0.1339    2.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9410   -1.0078    0.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7629   -2.2797   -0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5463   -1.5067    3.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7501   -2.7510    2.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6919   -1.2901    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8312   -4.4967    2.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6079   -3.2517    2.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5524   -4.2348    1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6029   -2.8997    0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7816   -0.8102   -1.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0024   -0.9466   -3.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9038    0.3477   -1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8882    1.3263    0.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9741    1.5038    2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  2  0
  4  2  2  3
 23 22  2  0
  2  1  1  0
 26 24  2  0
 24 25  1  0
 24 23  1  0
 20 21  1  0
 26 27  1  0
 27 28  2  0
 19 17  1  0
 17 18  2  0
 17 16  1  0
  2  3  1  0
 16 15  2  0
  6  7  1  0
 15 27  1  0
  7  8  1  0
 26 19  1  0
  8 10  1  0
 15  6  1  0
 10 11  1  0
 11 12  1  0
  6  5  1  0
  8  9  2  0
 22 20  1  0
 11 13  1  0
  5  4  1  0
 11 14  1  6
 23 51  1  0
 22 50  1  0
 16 48  1  0
  6 38  1  1
  5 36  1  0
  5 37  1  0
  4 35  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 25 52  1  0
 21 49  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
 10 39  1  0
 10 40  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
b-Hydroxyisovalerylshikonin	Generator
Β-hydroxyisovalerylshikonin	Generator
beta-HIVS	MeSH

Chemical Formula

C₂₁H₂₄O₇

Average Mass

388.4160 Da

Monoisotopic Mass

388.15220 Da

IUPAC Name

(1R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-hydroxy-3-methylbutanoate

Traditional Name

(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-hydroxy-3-methylbutanoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C(=O)C([H])=C(C(=O)C2=C(O[H])C([H])=C1[H])[C@]([H])(OC(=O)C([H])([H])C(O[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H24O7/c1-11(2)5-8-16(28-17(25)10-21(3,4)27)12-9-15(24)18-13(22)6-7-14(23)19(18)20(12)26/h5-7,9,16,22-23,27H,8,10H2,1-4H3/t16-/m1/s1

InChI Key

MXANJRGHSFELEJ-MRXNPFEDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Echium plantagineum	LOTUS Database	35616633
Lithospermum erythrorhizon	LOTUS Database	35616633
Onosma paniculata	JEOL database	Kretschmer, N., et al, J. Nat. Prod. 75, 865 (2012)

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
Fatty acid ester
Fatty acyl
Vinylogous acid
Tertiary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Alcohol
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	2.59	ALOGPS
logP	3.57	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	104.43 m³·mol⁻¹	ChemAxon
Polarizability	40.11 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

420738

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

479502

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Munni YA, Ali MC, Selsi NJ, Sultana M, Hossen M, Bipasha TH, Rahman M, Uddin MN, Hosen SMZ, Dash R: Molecular simulation studies to reveal the binding mechanisms of shikonin derivatives inhibiting VEGFR-2 kinase. Comput Biol Chem. 2021 Feb;90:107414. doi: 10.1016/j.compbiolchem.2020.107414. Epub 2020 Nov 4. [PubMed:33191109 ]
Chen X, Gu M, Jin J, Ren C, Pan Z, Wu Y, Tian N, Wu A, Sun L, Gao W, Wang X, Bei C, Zhou Y, Zhang X: beta-Hydroxyisovalerylshikonin inhibits IL-1beta-induced chondrocyte inflammation via Nrf2 and retards osteoarthritis in mice. Food Funct. 2020 Nov 18;11(11):10219-10230. doi: 10.1039/d0fo02192j. [PubMed:33169745 ]
Oshikiri H, Watanabe B, Yamamoto H, Yazaki K, Takanashi K: Two BAHD Acyltransferases Catalyze the Last Step in the Shikonin/Alkannin Biosynthetic Pathway. Plant Physiol. 2020 Oct;184(2):753-761. doi: 10.1104/pp.20.00207. Epub 2020 Jul 29. [PubMed:32727911 ]
Liang JW, Li T, Wang RS, Zhou L, Yang Q, Wang S, Guo LP: [Establishment of RNA interfered hairy root system of two CYP450 genes in Arnebia euchroma and its influence]. Zhongguo Zhong Yao Za Zhi. 2020 Jul;45(14):3422-3431. doi: 10.19540/j.cnki.cjcmm.20200506.110. [PubMed:32726058 ]
Vukic MD, Vukovic NL, Obradovic A, Matic M, Djukic M, Avdovic E: Redox status, DNA and HSA binding study of naturally occurring naphthoquinone derivatives. EXCLI J. 2020 Jan 3;19:48-70. doi: 10.17179/excli2019-1859. eCollection 2020. [PubMed:32038116 ]
Vukic MD, Vukovic NL, Djelic GT, Popovic SL, Zaric MM, Baskic DD, Krstic GB, Tesevic VV, Kacaniova MM: Antibacterial and cytotoxic activities of naphthoquinone pigments from Onosma visianii Clem. EXCLI J. 2017 Feb 16;16:73-88. doi: 10.17179/excli2016-762. eCollection 2017. [PubMed:28435429 ]
Koike A, Shibano M, Mori H, Kohama K, Fujimori K, Amano F: Simultaneous Addition of Shikonin and Its Derivatives with Lipopolysaccharide Induces Rapid Macrophage Death. Biol Pharm Bull. 2016;39(6):969-76. doi: 10.1248/bpb.b15-00948. [PubMed:27251498 ]
Ha JH, Jang J, Chung SI, Yoon Y: AMPK and SREBP-1c mediate the anti-adipogenic effect of beta-hydroxyisovalerylshikonin. Int J Mol Med. 2016 Mar;37(3):816-24. doi: 10.3892/ijmm.2016.2484. Epub 2016 Feb 8. [PubMed:26865314 ]
Jayasooriya RG, Lee KT, Lee HJ, Choi YH, Jeong JW, Kim GY: Anti-inflammatory effects of beta-hydroxyisovalerylshikonin in BV2 microglia are mediated through suppression of the PI3K/Akt/NF-kB pathway and activation of the Nrf2/HO-1 pathway. Food Chem Toxicol. 2014 Mar;65:82-9. doi: 10.1016/j.fct.2013.12.011. Epub 2013 Dec 21. [PubMed:24365262 ]
Authors unspecified: Retraction notice to "beta-Hydroxyisovalerylshikonin has a profound anti- growth activity in human endometrial and ovarian cancer cells" [Gynecol. Oncol. 109 (2008) 107-114]. Gynecol Oncol. 2013 Apr;129(1):269. doi: 10.1016/j.ygyno.2012.09.023. [PubMed:23638460 ]
Kretschmer, N., et al. (2012). Kretschmer, N., et al, J. Nat. Prod. 75, 865 (2012). J. Nat. Prod..

Showing NP-Card for beta-hydroxyisovalerylshikonin (NP0036680)

MOL for NP0036680 (beta-hydroxyisovalerylshikonin)

3D MOL for NP0036680 (beta-hydroxyisovalerylshikonin)

3D SDF for NP0036680 (beta-hydroxyisovalerylshikonin)

3D-SDF for NP0036680 (beta-hydroxyisovalerylshikonin)

PDB for NP0036680 (beta-hydroxyisovalerylshikonin)

3D PDB for NP0036680 (beta-hydroxyisovalerylshikonin)

SMILES for NP0036680 (beta-hydroxyisovalerylshikonin)

INCHI for NP0036680 (beta-hydroxyisovalerylshikonin)

Structure for NP0036680 (beta-hydroxyisovalerylshikonin)

3D Structure for NP0036680 (beta-hydroxyisovalerylshikonin)