Hypericin

Details

• Internal ID: 073a7557-e1d8-4ffd-9c80-178e6d1bc733
• Taxonomy: Benzenoids > Pyrenes > Benzopyrenes
• IUPAC Name: 9,11,13,16,18,20-hexahydroxy-5,24-dimethyloctacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(26),2,4(25),5,8,10,12,14(28),15(27),16,18,20,23-tridecaene-7,22-dione
• SMILES (Canonical): CC1=CC(=O)C2=C(C3=C(C=C(C4=C3C5=C2C1=C6C(=CC(=O)C7=C(C8=C(C=C(C4=C8C5=C67)O)O)O)C)O)O)O
• SMILES (Isomeric): CC1=CC(=O)C2=C(C3=C(C=C(C4=C3C5=C2C1=C6C(=CC(=O)C7=C(C8=C(C=C(C4=C8C5=C67)O)O)O)C)O)O)O
• InChI: 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/h3-6,33-38H,1-2H3
• InChI Key: YDOIFHVUBCIUHF-UHFFFAOYSA-N
• Popularity: 1,598 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₁₆O₈
• Molecular Weight: 504.40 g/mol
• Exact Mass: 504.08451746 g/mol
• Topological Polar Surface Area (TPSA): 156.00 Ų
• XlogP: 5.70

Synonyms

• 548-04-9
• Hypericum red
• hipericin
• hipericina
• hypericine
• Hyperizin
• Cyclosan
• Mycoporphyrin
• SGX301
• 1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione
• Cyclo-Werol
• VIMRxyn
• Hypericin [USAN]
• SGX-301
• Hypericin (SGX301)
• 4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethylnaphthodianthrone
• NSC407313
• Hypericin & Visible light
• NSC-407313
• CHEBI:5835
• CHEMBL286494
• 7V2F1075HD
• NSC622946
• 1372719-41-9
• 1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro(1,10,9,8-opqra)perylene-7,14-dione
• Phenanthro[1,10,9,8-opqra]perylene-7,14-dione, 1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-
• 9,11,13,16,18,20-hexahydroxy-5,24-dimethyloctacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(26),2,4(25),5,8,10,12,14(28),15(27),16,18,20,23-tridecaene-7,22-dione
• hexahydroxy(dimethyl)[?]dione
• 1:6:8:10:11:13-hexahydroxy-3:4-dimethyl-meso-naphthodianthrene-7:14-dione
• C30H16O8
• Phenanthro(1,10,9,8-opqra)perylene-7,14-dione, 1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-
• 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
• EINECS 208-941-0
• NSC 407313
• NSC 622946
• UNII-7V2F1075HD
• Cyclo werro
• CCRIS 8166
• hypericin [INN]
• (component of) Hypericum spp (st. John's wort)
• MFCD00016683
• BiomolKI_000032
• 4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethyl-mesonapthtodianthron
• BiomolKI2_000040
• HYPERICIN [WHO-DD]
• SCHEMBL3182
• BIDD:PXR0084
• BMK1-D8
• CHEMBL5082596
• SCHEMBL10262695
• DTXSID40203270
• BTXNYTINYBABQR-UHFFFAOYSA-N
• Hypericin - CAS 548-04-9
• Hypericin from Hypericum perforatum
• HY-N0453
• BDBM50060874
• CCG-36081
• HB3934
• HSCI1_000202
• LMPK13040001
• WHO 11835
• AKOS015895658
• AC-6048
• CS-5687
• NSC-622946
• NCGC00162454-01
• NCGC00163378-01
• NCGC00163378-02
• AS-74733
• NCI60_003879
• NCI60_006799
• FT-0627169
• C07606
• M01850
• A870351
• SR-05000002344
• Hypericin from Hypericum perforatum, ~95% (HPLC)
• Hypericin, primary pharmaceutical reference standard
• Q-100618
• SR-05000002344-2
• BRD-K29673530-001-03-9
• Z1736866019
• Hypericin is known as an anthroquinone derivative found in St. John's Wort.
• 1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione, 9CI
• 1,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro [1,10,9,8-opqra]perylene-7,14-dione P-conformer
• 5,7,11,18,22,24-HEXAHYDROXY-13,16-DIMETHYLOCTACYCLO[13.11.1.1(2),(1)?.0(3),?.0?,(2)?.0(1)?,(2)?.0(2)(1),(2)?.0(1)?,(2)?]OCTACOSA-1,3,5,7,10,12,14(28),15(27),16,18,21,23,25-TRIDECAENE-9,20-DIONE
• InChI=1/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,1-2H
• Phenanthro[1,10,9,8-opqra]perylene-7,14-dione,1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-, stereoisomer
• Phenanthro[1,9,8-opqra]perylene-7,14-dione,1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-, stereoisomer
• rac-(3aM,10aM)-1,3,4,6,8,13-hexahydroxy-10,11- dimethylphenanthro[1,10,9,8-opqra]perylene-7,14- dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.15%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	93.36%	91.49%
CHEMBL2581	P07339	Cathepsin D	91.85%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.68%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.44%	94.73%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.15%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.43%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.55%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.28%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.77%	99.15%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.34%	93.65%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.26%	86.33%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.89%	94.42%
CHEMBL1937	Q92769	Histone deacetylase 2	80.42%	94.75%

Plants that contains it

• Fagopyrum esculentum
• Hypericum adenotrichum
• Hypericum grandifolium
• Hypericum hirsutum
• Hypericum maculatum
• Hypericum montanum
• Hypericum perforatum
• Hypericum tetrapterum
• Hypericum triquetrifolium
• Hypericum venustum
• Rumex thianschanicus

Cross-Links

• PubChem: 3663
• LOTUS: LTS0238040
• wikiData: Q77509624