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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:04:32 UTC

Update Date

2022-03-07 02:54:02 UTC

HMDB ID

HMDB0034271

Secondary Accession Numbers

HMDB34271

Metabolite Identification

Common Name

Hypericin

Description

Hypericin is found in alcoholic beverages. Hypericin is widespread in Hypericum species especially Hypericum perforatum (St John's Wort) Hypericin is a red-coloured anthraquinone-derivative, which, together with hyperforin, is one of the principal active constituents of Hypericum (Saint John's wort). Hypericin is believed to act as an antibiotic and non-specific kinase inhibitor. Hypericin may inhibit the action of the enzyme dopamine -hydroxylase, leading to increased dopamine levels, although thus possibly decreasing norepinephrine and epinephrine

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061307412D          

 38 45  0  0  0  0            999 V2000
    0.1744    4.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    5.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    4.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    5.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    4.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    1.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    4.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    3.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    2.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    3.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3657    1.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    6.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4951    0.7048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.3284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946   -0.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
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  8  4  2  0  0  0  0
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 36 14  1  0  0  0  0
 37 29  2  0  0  0  0
 38 30  2  0  0  0  0
M  END

HMDB0034271
     RDKit          3D
Hypericin
 54 61  0  0  0  0  0  0  0  0999 V2000
    4.0749   -0.5505    1.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2817   -0.9974    0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5478   -2.3219    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5837   -3.0902   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8196   -4.3944   -0.5975 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -2.5213   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3595   -3.3103   -1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6246   -4.4815   -1.3294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810   -2.7601   -1.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8861   -3.5465   -1.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351   -4.8489   -2.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342   -3.0625   -1.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699   -1.7394   -1.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7483   -1.3879   -1.8798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086   -0.9525   -1.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7752    0.3597   -0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0024    0.9046   -0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0733    0.2773   -1.4300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2146    2.2439   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184    2.9789    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4674    4.2971    0.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9681    2.4494    0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9915    3.2332    0.7970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2147    4.4303    1.1285 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2665    2.7138    0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2554    3.5205    1.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9570    4.8222    1.8652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5240    3.0093    1.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8035    1.6874    1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2455    1.4856    0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8276    0.8759    0.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0757   -0.4311    0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -1.2448   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1948   -0.6777   -0.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2031   -1.4594   -0.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4648    0.6162    0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5064    1.4247    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327    1.1373   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5649    0.0442    2.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9541   -1.5530    2.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1430   -0.6225    1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5458   -2.7193    0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6718   -4.8876   -0.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2124   -5.4916   -2.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -3.7132   -2.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4340   -2.0220   -2.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9896    0.7219   -1.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2153    2.6309   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3607    4.7449    0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6194    5.4833    2.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3498    3.5979    2.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0077    1.7482    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4129    0.8578   -0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3702    2.4908    0.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
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 36 38  1  0
 32  2  1  0
 33  6  1  0
 35  9  2  0
 35 15  1  0
 38 16  2  0
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 37 31  1  0
  1 39  1  0
  1 40  1  0
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  3 42  1  0
  5 43  1  0
 11 44  1  0
 12 45  1  0
 14 46  1  0
 18 47  1  0
 19 48  1  0
 21 49  1  0
 27 50  1  0
 28 51  1  0
 30 52  1  0
 30 53  1  0
 30 54  1  0
M  END


  Mrv0541 05061307412D          

 38 45  0  0  0  0            999 V2000
    0.1744    4.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    5.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    4.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    5.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    4.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    1.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9845    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    4.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    3.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6850    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8748    3.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    4.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    1.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    6.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4951    0.7048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.3284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946   -0.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753    4.1348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.7048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4951    5.0702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
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  8  4  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
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 25 17  2  0  0  0  0
 25 21  1  0  0  0  0
 26 18  2  0  0  0  0
 26 22  1  0  0  0  0
 27 23  2  0  0  0  0
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 28 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 19  1  0  0  0  0
 29 21  1  0  0  0  0
 30 20  1  0  0  0  0
 30 22  1  0  0  0  0
 31  9  1  0  0  0  0
 32 10  1  0  0  0  0
 33 11  1  0  0  0  0
 34 12  1  0  0  0  0
 35 13  1  0  0  0  0
 36 14  1  0  0  0  0
 37 29  2  0  0  0  0
 38 30  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034271

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C4=C3C3=C2C1=C1C(C)=CC(O)=C2C(=O)C5=C(O)C=C(O)C4=C5C3=C12

> <INCHI_IDENTIFIER>
InChI=1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3

> <INCHI_KEY>
BTXNYTINYBABQR-UHFFFAOYSA-N

> <FORMULA>
C30H16O8

> <MOLECULAR_WEIGHT>
504.4432

> <EXACT_MASS>
504.084517488

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
50.95649342842092

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7,11,18,22,24-hexahydroxy-13,16-dimethyloctacyclo[13.11.1.1²,¹⁰.0³,⁸.0⁴,²⁵.0¹⁹,²⁷.0²¹,²⁶.0¹⁴,²⁸]octacosa-1(27),2(28),3,5,7,10,12,14,16,18,21,23,25-tridecaene-9,20-dione

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
7.698294890666666

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
2.1179088207448276

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3879350822145318

> <JCHEM_PKA_STRONGEST_BASIC>
16.114078792380027

> <JCHEM_POLAR_SURFACE_AREA>
155.52

> <JCHEM_REFRACTIVITY>
139.3118

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hypericin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034271
     RDKit          3D
Hypericin
 54 61  0  0  0  0  0  0  0  0999 V2000
    4.0749   -0.5505    1.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2817   -0.9974    0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5478   -2.3219    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5837   -3.0902   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8196   -4.3944   -0.5975 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -2.5213   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3595   -3.3103   -1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6246   -4.4815   -1.3294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810   -2.7601   -1.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8861   -3.5465   -1.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351   -4.8489   -2.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342   -3.0625   -1.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699   -1.7394   -1.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7483   -1.3879   -1.8798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086   -0.9525   -1.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7752    0.3597   -0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0024    0.9046   -0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0733    0.2773   -1.4300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2146    2.2439   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184    2.9789    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4674    4.2971    0.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9681    2.4494    0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9915    3.2332    0.7970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2147    4.4303    1.1285 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2665    2.7138    0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2554    3.5205    1.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9570    4.8222    1.8652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5240    3.0093    1.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8035    1.6874    1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2455    1.4856    0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8276    0.8759    0.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0757   -0.4311    0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -1.2448   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1948   -0.6777   -0.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2031   -1.4594   -0.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4648    0.6162    0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5064    1.4247    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327    1.1373   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5649    0.0442    2.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9541   -1.5530    2.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1430   -0.6225    1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5458   -2.7193    0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6718   -4.8876   -0.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2124   -5.4916   -2.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -3.7132   -2.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4340   -2.0220   -2.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9896    0.7219   -1.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2153    2.6309   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3607    4.7449    0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6194    5.4833    2.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3498    3.5979    2.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0077    1.7482    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4129    0.8578   -0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3702    2.4908    0.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 34 36  1  0
 36 37  2  0
 36 38  1  0
 32  2  1  0
 33  6  1  0
 35  9  2  0
 35 15  1  0
 38 16  2  0
 38 22  1  0
 37 25  1  0
 37 31  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  5 43  1  0
 11 44  1  0
 12 45  1  0
 14 46  1  0
 18 47  1  0
 19 48  1  0
 21 49  1  0
 27 50  1  0
 28 51  1  0
 30 52  1  0
 30 53  1  0
 30 54  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.326   8.300   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   9.464   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.179   5.681   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.854  10.338   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.870   0.442   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.903   5.099   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.830   6.845   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.846   9.173   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.326   4.226   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.366  10.047   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.879   1.607   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.895   3.935   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.358   0.733   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.399   6.554   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.342   6.554   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.350   7.718   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.374   3.062   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.383   4.226   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.838   3.935   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.870   8.591   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.854   2.189   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.887   6.845   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.846   5.099   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.862   7.427   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.862   3.353   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.879   5.681   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.358   4.808   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.366   5.972   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.342   2.480   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.383   8.300   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.683   3.062   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.374  11.211   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       8.391   1.316   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       9.399   2.480   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.350  -0.431   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      10.407   7.718   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       1.334   1.316   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       8.391   9.464   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    7    9                                                       
CONECT    4    8   10                                                       
CONECT    5   11   13                                                       
CONECT    6   12   14                                                       
CONECT    7    1    3   15                                                  
CONECT    8    2    4   16                                                  
CONECT    9    3   19   31                                                  
CONECT   10    4   20   32                                                  
CONECT   11    5   17   33                                                  
CONECT   12    6   18   34                                                  
CONECT   13    5   21   35                                                  
CONECT   14    6   22   36                                                  
CONECT   15    7   16   23                                                  
CONECT   16    8   15   24                                                  
CONECT   17   11   18   25                                                  
CONECT   18   12   17   26                                                  
CONECT   19    9   23   29                                                  
CONECT   20   10   24   30                                                  
CONECT   21   13   25   29                                                  
CONECT   22   14   26   30                                                  
CONECT   23   15   19   27                                                  
CONECT   24   16   20   28                                                  
CONECT   25   17   21   27                                                  
CONECT   26   18   22   28                                                  
CONECT   27   23   25   28                                                  
CONECT   28   24   26   27                                                  
CONECT   29   19   21   37                                                  
CONECT   30   20   22   38                                                  
CONECT   31    9                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   29                                                            
CONECT   38   30                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   90    0
END

COMPND    HMDB0034271
HETATM    1  C1  UNL     1       4.075  -0.550   1.982  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.282  -0.997   0.751  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.548  -2.322   0.387  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.584  -3.090  -0.221  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.820  -4.394  -0.597  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.342  -2.521  -0.455  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.359  -3.310  -1.017  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.625  -4.481  -1.329  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.881  -2.760  -1.208  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.886  -3.547  -1.767  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.535  -4.849  -2.103  1.00  0.00           O  
HETATM   12  C9  UNL     1      -3.134  -3.063  -1.971  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.470  -1.739  -1.624  1.00  0.00           C  
HETATM   14  O4  UNL     1      -4.748  -1.388  -1.880  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.509  -0.953  -1.078  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.775   0.360  -0.703  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.002   0.905  -0.893  1.00  0.00           C  
HETATM   18  O5  UNL     1      -5.073   0.277  -1.430  1.00  0.00           O  
HETATM   19  C14 UNL     1      -4.215   2.244  -0.506  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.218   2.979   0.045  1.00  0.00           C  
HETATM   21  O6  UNL     1      -3.467   4.297   0.413  1.00  0.00           O  
HETATM   22  C16 UNL     1      -1.968   2.449   0.246  1.00  0.00           C  
HETATM   23  C17 UNL     1      -0.992   3.233   0.797  1.00  0.00           C  
HETATM   24  O7  UNL     1      -1.215   4.430   1.128  1.00  0.00           O  
HETATM   25  C18 UNL     1       0.266   2.714   0.999  1.00  0.00           C  
HETATM   26  C19 UNL     1       1.255   3.521   1.511  1.00  0.00           C  
HETATM   27  O8  UNL     1       0.957   4.822   1.865  1.00  0.00           O  
HETATM   28  C20 UNL     1       2.524   3.009   1.660  1.00  0.00           C  
HETATM   29  C21 UNL     1       2.803   1.687   1.304  1.00  0.00           C  
HETATM   30  C22 UNL     1       4.245   1.486   0.837  1.00  0.00           C  
HETATM   31  C23 UNL     1       1.828   0.876   0.826  1.00  0.00           C  
HETATM   32  C24 UNL     1       2.076  -0.431   0.491  1.00  0.00           C  
HETATM   33  C25 UNL     1       1.060  -1.245  -0.121  1.00  0.00           C  
HETATM   34  C26 UNL     1      -0.195  -0.678  -0.300  1.00  0.00           C  
HETATM   35  C27 UNL     1      -1.203  -1.459  -0.866  1.00  0.00           C  
HETATM   36  C28 UNL     1      -0.465   0.616   0.079  1.00  0.00           C  
HETATM   37  C29 UNL     1       0.506   1.425   0.644  1.00  0.00           C  
HETATM   38  C30 UNL     1      -1.733   1.137  -0.124  1.00  0.00           C  
HETATM   39  H1  UNL     1       3.565   0.044   2.718  1.00  0.00           H  
HETATM   40  H2  UNL     1       3.954  -1.553   2.641  1.00  0.00           H  
HETATM   41  H3  UNL     1       5.143  -0.623   1.899  1.00  0.00           H  
HETATM   42  H4  UNL     1       4.546  -2.719   0.603  1.00  0.00           H  
HETATM   43  H5  UNL     1       3.672  -4.888  -0.475  1.00  0.00           H  
HETATM   44  H6  UNL     1      -2.212  -5.492  -2.518  1.00  0.00           H  
HETATM   45  H7  UNL     1      -3.898  -3.713  -2.414  1.00  0.00           H  
HETATM   46  H8  UNL     1      -5.434  -2.022  -2.293  1.00  0.00           H  
HETATM   47  H9  UNL     1      -5.990   0.722  -1.560  1.00  0.00           H  
HETATM   48  H10 UNL     1      -5.215   2.631  -0.678  1.00  0.00           H  
HETATM   49  H11 UNL     1      -4.361   4.745   0.293  1.00  0.00           H  
HETATM   50  H12 UNL     1       1.619   5.483   2.246  1.00  0.00           H  
HETATM   51  H13 UNL     1       3.350   3.598   2.056  1.00  0.00           H  
HETATM   52  H14 UNL     1       5.008   1.748   1.548  1.00  0.00           H  
HETATM   53  H15 UNL     1       4.413   0.858  -0.020  1.00  0.00           H  
HETATM   54  H16 UNL     1       4.370   2.491   0.182  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3    3   32
CONECT    3    4   42
CONECT    4    5    6    6
CONECT    5   43
CONECT    6    7   33
CONECT    7    8    8    9
CONECT    9   10   35   35
CONECT   10   11   12   12
CONECT   11   44
CONECT   12   13   45
CONECT   13   14   15   15
CONECT   14   46
CONECT   15   16   35
CONECT   16   17   38   38
CONECT   17   18   19   19
CONECT   18   47
CONECT   19   20   48
CONECT   20   21   22   22
CONECT   21   49
CONECT   22   23   38
CONECT   23   24   24   25
CONECT   25   26   26   37
CONECT   26   27   28
CONECT   27   50
CONECT   28   29   29   51
CONECT   29   30   31
CONECT   30   52   53   54
CONECT   31   32   32   37
CONECT   32   33
CONECT   33   34   34
CONECT   34   35   36
CONECT   36   37   37   38
END

HMDB0034271
     RDKit          3D
Hypericin
 54 61  0  0  0  0  0  0  0  0999 V2000
    4.0749   -0.5505    1.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2817   -0.9974    0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5478   -2.3219    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5837   -3.0902   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8196   -4.3944   -0.5975 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -2.5213   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3595   -3.3103   -1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6246   -4.4815   -1.3294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810   -2.7601   -1.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8861   -3.5465   -1.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351   -4.8489   -2.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342   -3.0625   -1.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699   -1.7394   -1.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7483   -1.3879   -1.8798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086   -0.9525   -1.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7752    0.3597   -0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0024    0.9046   -0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0733    0.2773   -1.4300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2146    2.2439   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184    2.9789    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4674    4.2971    0.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9681    2.4494    0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9915    3.2332    0.7970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2147    4.4303    1.1285 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2665    2.7138    0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2554    3.5205    1.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9570    4.8222    1.8652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5240    3.0093    1.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8035    1.6874    1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2455    1.4856    0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8276    0.8759    0.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0757   -0.4311    0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -1.2448   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1948   -0.6777   -0.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2031   -1.4594   -0.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4648    0.6162    0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5064    1.4247    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327    1.1373   -0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5649    0.0442    2.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9541   -1.5530    2.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1430   -0.6225    1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5458   -2.7193    0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6718   -4.8876   -0.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2124   -5.4916   -2.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -3.7132   -2.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4340   -2.0220   -2.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9896    0.7219   -1.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2153    2.6309   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3607    4.7449    0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6194    5.4833    2.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3498    3.5979    2.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0077    1.7482    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4129    0.8578   -0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3702    2.4908    0.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
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  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  5 43  1  0
 11 44  1  0
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 18 47  1  0
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 27 50  1  0
 28 51  1  0
 30 52  1  0
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 30 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1:6:8:10:11:13-Hexahydroxy-3:4-dimethyl-meso-naphthodianthrene-7:14-dione	ChEBI
Hipericina	ChEBI
Hypericine	ChEBI
Hypericum red	ChEBI
Hyperizin	ChEBI
1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione, 9ci	HMDB
4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethylnaphthodianthrone	HMDB
Hypericin & visible light	HMDB
Hypericin from hypericum perforatum	HMDB
Hypericum extract	HMDB
Mycoporphyrin	HMDB
Vimrxyn	HMDB
mono-(123I)iodohypericin	MeSH

Chemical Formula

C₃₀H₁₆O₈

Average Molecular Weight

504.4432

Monoisotopic Molecular Weight

504.084517488

IUPAC Name

5,7,11,18,22,24-hexahydroxy-13,16-dimethyloctacyclo[13.11.1.1²,¹⁰.0³,⁸.0⁴,²⁵.0¹⁹,²⁷.0²¹,²⁶.0¹⁴,²⁸]octacosa-1(27),2(28),3,5,7,10,12,14,16,18,21,23,25-tridecaene-9,20-dione

Traditional Name

hypericin

CAS Registry Number

548-04-9

SMILES

CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C4=C3C3=C2C1=C1C(C)=CC(O)=C2C(=O)C5=C(O)C=C(O)C4=C5C3=C12

InChI Identifier

InChI=1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3

InChI Key

BTXNYTINYBABQR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Benzo-a-pyrene
Benzo-e-pyrene
Phenanthro-perylenequinone
Perylenequinone
Chrysene
Triphenylene
Phenanthrol
Phenanthrene
Anthracene
1-naphthol
2-naphthol
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Polyol
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

carbopolycyclic compound (CHEBI:5835 )
Anthracenes and phenanthrenes (C07606 )
Anthrone type (C07606 )
Anthracenes and phenanthrenes (LMPK13040001 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034271)
Cell membrane (HMDB: HMDB0034271)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034271)

Source

Exogenous

Exogenous (HMDB: HMDB0034271)

Food

Food (HMDB: HMDB0034271)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0034271)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antimicrobial agent

Antiviral

Antiviral (HMDB: HMDB0034271)

Pharmaceutical (HMDB: HMDB0034271)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antidepressant (HMDB: HMDB0034271)

Biological role

Nutrient (HMDB: HMDB0034271)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	300 °C	Not Available
Boiling Point	1020.33 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	6.3e-06 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	10.827 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0073 g/L	ALOGPS
logP	3.92	ALOGPS
logP	7.7	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	1.39	ChemAxon
pKa (Strongest Basic)	16.11	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	139.31 m³·mol⁻¹	ChemAxon
Polarizability	50.96 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	213.206	31661259
DarkChem	[M-H]-	206.14	31661259
DeepCCS	[M-2H]-	248.273	30932474
DeepCCS	[M+Na]+	222.946	30932474
AllCCS	[M+H]+	213.0	32859911
AllCCS	[M+H-H2O]+	211.1	32859911
AllCCS	[M+NH4]+	214.8	32859911
AllCCS	[M+Na]+	215.4	32859911
AllCCS	[M-H]-	210.9	32859911
AllCCS	[M+Na-2H]-	210.1	32859911
AllCCS	[M+HCOO]-	209.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.44 minutes	32390414
Predicted by Siyang on May 30, 2022	15.8004 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.9 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3498.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	270.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	116.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	153.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	402.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	782.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	625.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	90.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	967.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	557.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2397.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	393.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	535.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	570.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	129.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	221.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hypericin	CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C4=C3C3=C2C1=C1C(C)=CC(O)=C2C(=O)C5=C(O)C=C(O)C4=C5C3=C12	7322.1	Standard polar	33892256
Hypericin	CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C4=C3C3=C2C1=C1C(C)=CC(O)=C2C(=O)C5=C(O)C=C(O)C4=C5C3=C12	2921.7	Standard non polar	33892256
Hypericin	CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C4=C3C3=C2C1=C1C(C)=CC(O)=C2C(=O)C5=C(O)C=C(O)C4=C5C3=C12	5605.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hypericin,1TMS,isomer #1	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5304.1	Semi standard non polar	33892256
Hypericin,1TMS,isomer #2	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5298.7	Semi standard non polar	33892256
Hypericin,1TMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5310.9	Semi standard non polar	33892256
Hypericin,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5294.0	Semi standard non polar	33892256
Hypericin,2TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5288.1	Semi standard non polar	33892256
Hypericin,2TMS,isomer #3	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5292.3	Semi standard non polar	33892256
Hypericin,2TMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5293.5	Semi standard non polar	33892256
Hypericin,2TMS,isomer #5	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5294.0	Semi standard non polar	33892256
Hypericin,2TMS,isomer #6	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5281.6	Semi standard non polar	33892256
Hypericin,2TMS,isomer #7	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5285.2	Semi standard non polar	33892256
Hypericin,2TMS,isomer #8	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5264.6	Semi standard non polar	33892256
Hypericin,2TMS,isomer #9	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5306.8	Semi standard non polar	33892256
Hypericin,3TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5181.1	Semi standard non polar	33892256
Hypericin,3TMS,isomer #10	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5175.6	Semi standard non polar	33892256
Hypericin,3TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5186.2	Semi standard non polar	33892256
Hypericin,3TMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5175.7	Semi standard non polar	33892256
Hypericin,3TMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5181.8	Semi standard non polar	33892256
Hypericin,3TMS,isomer #5	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5168.2	Semi standard non polar	33892256
Hypericin,3TMS,isomer #6	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5182.6	Semi standard non polar	33892256
Hypericin,3TMS,isomer #7	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5200.0	Semi standard non polar	33892256
Hypericin,3TMS,isomer #8	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5169.3	Semi standard non polar	33892256
Hypericin,3TMS,isomer #9	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5162.1	Semi standard non polar	33892256
Hypericin,4TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5083.0	Semi standard non polar	33892256
Hypericin,4TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5080.3	Semi standard non polar	33892256
Hypericin,4TMS,isomer #3	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5079.2	Semi standard non polar	33892256
Hypericin,4TMS,isomer #4	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5085.3	Semi standard non polar	33892256
Hypericin,4TMS,isomer #5	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5070.4	Semi standard non polar	33892256
Hypericin,4TMS,isomer #6	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5070.3	Semi standard non polar	33892256
Hypericin,4TMS,isomer #7	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5074.0	Semi standard non polar	33892256
Hypericin,4TMS,isomer #8	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5076.2	Semi standard non polar	33892256
Hypericin,4TMS,isomer #9	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5059.5	Semi standard non polar	33892256
Hypericin,5TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	4926.2	Semi standard non polar	33892256
Hypericin,5TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	4929.1	Semi standard non polar	33892256
Hypericin,5TMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C6=C1C2=C4C5=C36	4916.9	Semi standard non polar	33892256
Hypericin,1TBDMS,isomer #1	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5509.8	Semi standard non polar	33892256
Hypericin,1TBDMS,isomer #2	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5504.1	Semi standard non polar	33892256
Hypericin,1TBDMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5508.5	Semi standard non polar	33892256
Hypericin,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5698.1	Semi standard non polar	33892256
Hypericin,2TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5694.4	Semi standard non polar	33892256
Hypericin,2TBDMS,isomer #3	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5697.6	Semi standard non polar	33892256
Hypericin,2TBDMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5697.1	Semi standard non polar	33892256
Hypericin,2TBDMS,isomer #5	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5694.7	Semi standard non polar	33892256
Hypericin,2TBDMS,isomer #6	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5690.5	Semi standard non polar	33892256
Hypericin,2TBDMS,isomer #7	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5692.3	Semi standard non polar	33892256
Hypericin,2TBDMS,isomer #8	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5675.1	Semi standard non polar	33892256
Hypericin,2TBDMS,isomer #9	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5706.7	Semi standard non polar	33892256
Hypericin,3TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5776.2	Semi standard non polar	33892256
Hypericin,3TBDMS,isomer #10	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5755.6	Semi standard non polar	33892256
Hypericin,3TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5776.2	Semi standard non polar	33892256
Hypericin,3TBDMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5766.9	Semi standard non polar	33892256
Hypericin,3TBDMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5768.2	Semi standard non polar	33892256
Hypericin,3TBDMS,isomer #5	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5762.0	Semi standard non polar	33892256
Hypericin,3TBDMS,isomer #6	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5765.7	Semi standard non polar	33892256
Hypericin,3TBDMS,isomer #7	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5772.1	Semi standard non polar	33892256
Hypericin,3TBDMS,isomer #8	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C6=C1C2=C4C5=C36	5760.4	Semi standard non polar	33892256
Hypericin,3TBDMS,isomer #9	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C6=C1C2=C4C5=C36	5752.5	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13014

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hypericin

METLIN ID

Not Available

PubChem Compound

5281051

PDB ID

Not Available

ChEBI ID

5835

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1667711

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kang BY, Chung SW, Kim TS: Inhibition of interleukin-12 production in lipopolysaccharide-activated mouse macrophages by hpyericin, an active component of Hypericum perforatum. Planta Med. 2001 Jun;67(4):364-6. [PubMed:11458458 ]
Butterweck V, Christoffel V, Nahrstedt A, Petereit F, Spengler B, Winterhoff H: Step by step removal of hyperforin and hypericin: activity profile of different Hypericum preparations in behavioral models. Life Sci. 2003 Jun 20;73(5):627-39. [PubMed:12770617 ]
Park J, English DS, Wannemuehler Y, Carpenter S, Petrich JW: The role of oxygen in the antiviral activity of hypericin and hypocrellin. Photochem Photobiol. 1998 Oct;68(4):593-7. [PubMed:9796444 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Hypericin (HMDB0034271)

MOL for HMDB0034271 (Hypericin)

3D MOL for HMDB0034271 (Hypericin)

3D SDF for HMDB0034271 (Hypericin)

3D-SDF for HMDB0034271 (Hypericin)

PDB for HMDB0034271 (Hypericin)

3D PDB for HMDB0034271 (Hypericin)

SMILES for HMDB0034271 (Hypericin)

INCHI for HMDB0034271 (Hypericin)

Structure for HMDB0034271 (Hypericin)

3D Structure for HMDB0034271 (Hypericin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized