NP-MRD: Showing NP-Card for deoxyshikonin (NP0039224)

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Record Information

Version

2.0

Created at

2021-06-20 21:43:06 UTC

Updated at

2021-06-30 00:12:26 UTC

NP-MRD ID

NP0039224

Secondary Accession Numbers

None

Natural Product Identification

Common Name

deoxyshikonin

Provided By

JEOL Database JEOL Logo

Description

5,8-Dihydroxy-2-(4-methylpent-3-en-1-yl)-1,4-dihydronaphthalene-1,4-dione is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. deoxyshikonin is found in Alkanna cappadocica, Alkanna hirsutissima, Arnebia decumbens, Arnebia euchroma, Arnebia hispidissima, Bacteroides fragilis subsp. thetaotus and Lithospermum erythrorhizon. deoxyshikonin was first documented in 1994 (Meselhy, M. R., et al.). Based on a literature review very few articles have been published on 5,8-dihydroxy-2-(4-methylpent-3-en-1-yl)-1,4-dihydronaphthalene-1,4-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123433D          

 36 37  0  0  0  0            999 V2000
    0.3611   -0.9564    2.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841    0.2665    2.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5352    0.0937    3.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635    1.4360    1.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280    1.7933    0.7707 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0225    1.9036   -0.6164 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5937    0.6006   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106    0.3660   -1.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4636   -0.9148   -1.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6763   -1.0892   -1.7068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -1.9805   -2.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0114   -3.2289   -2.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3445   -3.5322   -2.5322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1301   -4.2413   -2.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440   -4.0134   -2.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292   -2.7741   -2.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912   -2.6344   -2.3685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523   -1.7498   -2.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3686   -0.4397   -1.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5788   -0.2324   -1.5736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2752   -1.8051    2.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0959   -0.8367    1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9062   -1.2144    3.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0658   -0.1530    4.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329    0.9995    3.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2206   -0.7160    3.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432    2.2478    2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738    1.1006    0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605    2.7682    1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8072    2.6717   -0.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    2.2731   -1.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6418    1.1041   -0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8624   -2.7419   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5139   -5.2063   -3.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367   -4.8000   -3.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101   -1.7185   -2.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
  7 19  1  0  0  0  0
 19 18  1  0  0  0  0
  7  6  1  0  0  0  0
 15 14  1  0  0  0  0
  6  5  1  0  0  0  0
 18 11  2  0  0  0  0
 19 20  2  0  0  0  0
 15 16  2  0  0  0  0
  9 10  2  0  0  0  0
 11  9  1  0  0  0  0
 16 17  1  0  0  0  0
 14 12  2  0  0  0  0
 12 13  1  0  0  0  0
  9  8  1  0  0  0  0
  5  4  1  0  0  0  0
 12 11  1  0  0  0  0
  4  2  2  3  0  0  0
  8  7  2  0  0  0  0
  2  1  1  0  0  0  0
 18 16  1  0  0  0  0
  2  3  1  0  0  0  0
 15 35  1  0  0  0  0
 14 34  1  0  0  0  0
  8 32  1  0  0  0  0
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
 17 36  1  0  0  0  0
 13 33  1  0  0  0  0
  4 27  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
M  END

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
    0.3611   -0.9564    2.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841    0.2665    2.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5352    0.0937    3.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635    1.4360    1.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280    1.7933    0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0225    1.9036   -0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937    0.6006   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106    0.3660   -1.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4636   -0.9148   -1.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6763   -1.0892   -1.7068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -1.9805   -2.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0114   -3.2289   -2.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3445   -3.5322   -2.5322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1301   -4.2413   -2.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440   -4.0134   -2.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292   -2.7741   -2.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912   -2.6344   -2.3685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523   -1.7498   -2.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3686   -0.4397   -1.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5788   -0.2324   -1.5736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2752   -1.8051    2.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0959   -0.8367    1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9062   -1.2144    3.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0658   -0.1530    4.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329    0.9995    3.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2206   -0.7160    3.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432    2.2478    2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738    1.1006    0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605    2.7682    1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8072    2.6717   -0.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    2.2731   -1.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6418    1.1041   -0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8624   -2.7419   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5139   -5.2063   -3.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367   -4.8000   -3.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101   -1.7185   -2.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
  7 19  1  0
 19 18  1  0
  7  6  1  0
 15 14  1  0
  6  5  1  0
 18 11  2  0
 19 20  2  0
 15 16  2  0
  9 10  2  0
 11  9  1  0
 16 17  1  0
 14 12  2  0
 12 13  1  0
  9  8  1  0
  5  4  1  0
 12 11  1  0
  4  2  2  3
  8  7  2  0
  2  1  1  0
 18 16  1  0
  2  3  1  0
 15 35  1  0
 14 34  1  0
  8 32  1  0
  6 30  1  0
  6 31  1  0
  5 28  1  0
  5 29  1  0
 17 36  1  0
 13 33  1  0
  4 27  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
M  END


  Mrv1652306202123433D          

 36 37  0  0  0  0            999 V2000
    0.3611   -0.9564    2.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841    0.2665    2.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5352    0.0937    3.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635    1.4360    1.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280    1.7933    0.7707 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0225    1.9036   -0.6164 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5937    0.6006   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106    0.3660   -1.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4636   -0.9148   -1.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6763   -1.0892   -1.7068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -1.9805   -2.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0114   -3.2289   -2.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3445   -3.5322   -2.5322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1301   -4.2413   -2.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440   -4.0134   -2.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292   -2.7741   -2.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912   -2.6344   -2.3685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523   -1.7498   -2.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3686   -0.4397   -1.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5788   -0.2324   -1.5736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2752   -1.8051    2.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0959   -0.8367    1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9062   -1.2144    3.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0658   -0.1530    4.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329    0.9995    3.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2206   -0.7160    3.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432    2.2478    2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738    1.1006    0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605    2.7682    1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8072    2.6717   -0.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    2.2731   -1.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6418    1.1041   -0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8624   -2.7419   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5139   -5.2063   -3.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367   -4.8000   -3.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101   -1.7185   -2.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
  7 19  1  0  0  0  0
 19 18  1  0  0  0  0
  7  6  1  0  0  0  0
 15 14  1  0  0  0  0
  6  5  1  0  0  0  0
 18 11  2  0  0  0  0
 19 20  2  0  0  0  0
 15 16  2  0  0  0  0
  9 10  2  0  0  0  0
 11  9  1  0  0  0  0
 16 17  1  0  0  0  0
 14 12  2  0  0  0  0
 12 13  1  0  0  0  0
  9  8  1  0  0  0  0
  5  4  1  0  0  0  0
 12 11  1  0  0  0  0
  4  2  2  3  0  0  0
  8  7  2  0  0  0  0
  2  1  1  0  0  0  0
 18 16  1  0  0  0  0
  2  3  1  0  0  0  0
 15 35  1  0  0  0  0
 14 34  1  0  0  0  0
  8 32  1  0  0  0  0
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
 17 36  1  0  0  0  0
 13 33  1  0  0  0  0
  4 27  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039224

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(O[H])C2=C1C(=O)C([H])=C(C2=O)C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O4/c1-9(2)4-3-5-10-8-13(19)14-11(17)6-7-12(18)15(14)16(10)20/h4,6-8,17-18H,3,5H2,1-2H3

> <INCHI_KEY>
VOMDIEGPEURZJO-UHFFFAOYSA-N

> <FORMULA>
C16H16O4

> <MOLECULAR_WEIGHT>
272.3

> <EXACT_MASS>
272.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.93616067564171

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,8-dihydroxy-2-(4-methylpent-3-en-1-yl)-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
4.242452071666666

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.307098819402862

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.523214591254282

> <JCHEM_PKA_STRONGEST_BASIC>
-5.564557566032307

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
78.30469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-deoxyalkannin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
    0.3611   -0.9564    2.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841    0.2665    2.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5352    0.0937    3.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635    1.4360    1.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280    1.7933    0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0225    1.9036   -0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937    0.6006   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106    0.3660   -1.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4636   -0.9148   -1.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6763   -1.0892   -1.7068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -1.9805   -2.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0114   -3.2289   -2.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3445   -3.5322   -2.5322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1301   -4.2413   -2.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440   -4.0134   -2.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292   -2.7741   -2.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912   -2.6344   -2.3685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523   -1.7498   -2.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3686   -0.4397   -1.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5788   -0.2324   -1.5736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2752   -1.8051    2.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0959   -0.8367    1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9062   -1.2144    3.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0658   -0.1530    4.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329    0.9995    3.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2206   -0.7160    3.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432    2.2478    2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738    1.1006    0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605    2.7682    1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8072    2.6717   -0.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    2.2731   -1.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6418    1.1041   -0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8624   -2.7419   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5139   -5.2063   -3.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367   -4.8000   -3.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101   -1.7185   -2.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
  7 19  1  0
 19 18  1  0
  7  6  1  0
 15 14  1  0
  6  5  1  0
 18 11  2  0
 19 20  2  0
 15 16  2  0
  9 10  2  0
 11  9  1  0
 16 17  1  0
 14 12  2  0
 12 13  1  0
  9  8  1  0
  5  4  1  0
 12 11  1  0
  4  2  2  3
  8  7  2  0
  2  1  1  0
 18 16  1  0
  2  3  1  0
 15 35  1  0
 14 34  1  0
  8 32  1  0
  6 30  1  0
  6 31  1  0
  5 28  1  0
  5 29  1  0
 17 36  1  0
 13 33  1  0
  4 27  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  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       0.361  -0.956   2.276  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.484   0.267   2.506  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.535   0.094   3.573  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.364   1.436   1.848  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.628   1.793   0.771  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.023   1.904  -0.616  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.594   0.601  -1.119  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.911   0.366  -1.182  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.464  -0.915  -1.651  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.676  -1.089  -1.707  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.528  -1.980  -2.043  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.011  -3.229  -2.462  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.345  -3.532  -2.532  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.130  -4.241  -2.833  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.244  -4.013  -2.791  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.729  -2.774  -2.378  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.091  -2.634  -2.369  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.152  -1.750  -2.001  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.369  -0.440  -1.564  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.579  -0.232  -1.574  0.00  0.00           O+0
HETATM   21  H   UNK     0      -0.275  -1.805   2.002  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.096  -0.837   1.477  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.906  -1.214   3.189  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.066  -0.153   4.531  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.133   1.000   3.719  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.221  -0.716   3.302  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.043   2.248   2.110  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.474   1.101   0.745  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.061   2.768   1.030  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.807   2.672  -0.586  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.721   2.273  -1.334  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.642   1.104  -0.869  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.862  -2.742  -2.257  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.514  -5.206  -3.155  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.937  -4.800  -3.080  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.310  -1.718  -2.082  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   24   25   26                                             
CONECT    4    5    2   27                                                  
CONECT    5    6    4   28   29                                             
CONECT    6    7    5   30   31                                             
CONECT    7   19    6    8                                                  
CONECT    8    9    7   32                                                  
CONECT    9   10   11    8                                                  
CONECT   10    9                                                            
CONECT   11   18    9   12                                                  
CONECT   12   14   13   11                                                  
CONECT   13   12   33                                                       
CONECT   14   15   12   34                                                  
CONECT   15   14   16   35                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   36                                                       
CONECT   18   19   11   16                                                  
CONECT   19    7   18   20                                                  
CONECT   20   19                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    6                                                            
CONECT   32    8                                                            
CONECT   33   13                                                            
CONECT   34   14                                                            
CONECT   35   15                                                            
CONECT   36   17                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

RDKit          3D

36 37  0  0  0  0  0  0  0  0999 V2000
    0.3611   -0.9564    2.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841    0.2665    2.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5352    0.0937    3.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635    1.4360    1.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280    1.7933    0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0225    1.9036   -0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937    0.6006   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106    0.3660   -1.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4636   -0.9148   -1.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6763   -1.0892   -1.7068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -1.9805   -2.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0114   -3.2289   -2.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3445   -3.5322   -2.5322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1301   -4.2413   -2.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440   -4.0134   -2.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292   -2.7741   -2.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912   -2.6344   -2.3685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523   -1.7498   -2.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3686   -0.4397   -1.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5788   -0.2324   -1.5736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2752   -1.8051    2.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0959   -0.8367    1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9062   -1.2144    3.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0658   -0.1530    4.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329    0.9995    3.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2206   -0.7160    3.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432    2.2478    2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738    1.1006    0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605    2.7682    1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8072    2.6717   -0.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    2.2731   -1.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6418    1.1041   -0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8624   -2.7419   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5139   -5.2063   -3.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367   -4.8000   -3.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101   -1.7185   -2.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
  7 19  1  0
 19 18  1  0
  7  6  1  0
 15 14  1  0
  6  5  1  0
 18 11  2  0
 19 20  2  0
 15 16  2  0
  9 10  2  0
 11  9  1  0
 16 17  1  0
 14 12  2  0
 12 13  1  0
  9  8  1  0
  5  4  1  0
 12 11  1  0
  4  2  2  3
  8  7  2  0
  2  1  1  0
 18 16  1  0
  2  3  1  0
 15 35  1  0
 14 34  1  0
  8 32  1  0
  6 30  1  0
  6 31  1  0
  5 28  1  0
  5 29  1  0
 17 36  1  0
 13 33  1  0
  4 27  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
11-Deoxyalkannin	ChEMBL

Chemical Formula

C₁₆H₁₆O₄

Average Mass

272.3000 Da

Monoisotopic Mass

272.10486 Da

IUPAC Name

5,8-dihydroxy-2-(4-methylpent-3-en-1-yl)-1,4-dihydronaphthalene-1,4-dione

Traditional Name

11-deoxyalkannin

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(O[H])C2=C1C(=O)C([H])=C(C2=O)C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C16H16O4/c1-9(2)4-3-5-10-8-13(19)14-11(17)6-7-12(18)15(14)16(10)20/h4,6-8,17-18H,3,5H2,1-2H3

InChI Key

VOMDIEGPEURZJO-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Alkanna cappadocica	LOTUS Database	35616633
Alkanna hirsutissima	LOTUS Database	35616633
Arnebia decumbens	LOTUS Database	35616633
Arnebia euchroma	LOTUS Database	35616633
Arnebia hispidissima	LOTUS Database	35616633
Bacteroides fragilis subsp. thetaotus	JEOL database	Meselhy, M. R., et al, Tetrahedron 50, 3081 (1994)
Lithospermum erythrorhizon	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthoquinones. These 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
Monoterpenoid
Bicyclic monoterpenoid
Aromatic monoterpenoid
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthoquinone (CHEBI:81530 )
a quinone (CPD-9321 )

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	2.74	ALOGPS
logP	4.24	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.52	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.3 m³·mol⁻¹	ChemAxon
Polarizability	27.94 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

89341

KEGG Compound ID

C18133

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Meselhy, M. R., et al. (1994). Meselhy, M. R., et al, Tetrahedron 50, 3081 (1994). Tetrahedron.

Showing NP-Card for deoxyshikonin (NP0039224)

MOL for NP0039224 (deoxyshikonin)

3D MOL for NP0039224 (deoxyshikonin)

3D SDF for NP0039224 (deoxyshikonin)

3D-SDF for NP0039224 (deoxyshikonin)

PDB for NP0039224 (deoxyshikonin)

3D PDB for NP0039224 (deoxyshikonin)

SMILES for NP0039224 (deoxyshikonin)

INCHI for NP0039224 (deoxyshikonin)

Structure for NP0039224 (deoxyshikonin)

3D Structure for NP0039224 (deoxyshikonin)