Natural Product (NP) Details

General Information of the NP (ID: NP4945)
Name
Hypericin
Synonyms
hypericin; 548-04-9; Hypericum red; hypericine; Cyclosan; hipericina; Hyperizin; Mycoporphyrin; 1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione; Cyclo-Werol; Hypericum Extract; VIMRxyn; UNII-7V2F1075HD; MFCD00016683; NSC407313; Hypericin & Visible light; 7V2F1075HD; NSC622946; Cyclo werrol; 4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethylnaphthodianthrone; 1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro(1,10,9,8-opqra)perylene-7,14-dione; hexahydroxy(dimethyl)[?]dione; 1:6:8:10:11:13-hexahydroxy-3:4-dimethyl-meso-naphthodianthrene-7:14-dione; Phenanthro[1,10,9,8-opqra]perylene-7,14-dione, 1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-; Phenanthro[1,10,9,8-opqra]perylene-7,14-dione,1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-, stereoisomer; C30H16O8; EINECS 208-941-0; NSC 407313; NSC 622946; CCRIS 8166; (component of) Hypericum spp (st. John's wort); BiomolKI_000032; 4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethyl-mesonapthtodianthron; BiomolKI2_000040; SCHEMBL3182; BIDD:PXR0084; BMK1-D8; SCHEMBL10262695; DTXSID40203270; Hypericin - CAS 548-04-9; Hypericin from Hypericum perforatum; HY-N0453; ZINC3780340; BDBM50060874; CCG-36081; HSCI1_000202; LMPK13040001; AKOS015895658; AC-6048; CS-5687; EBD2048972; MCULE-7319800130; NSC-622946; NCGC00162454-01; NCGC00163378-01; NCGC00163378-02; AS-74733; NCI60_003879; NCI60_006799; NCGC00163378-03!; FT-0627169; N2739; C07606; 33919-EP2275420A1; 33919-EP2295055A2; 33919-EP2295416A2; 33919-EP2298748A2; 33919-EP2298764A1; 33919-EP2298765A1; 33919-EP2305642A2; 33919-EP2311453A1; 548H049; SR-05000002344; Hypericin from Hypericum perforatum, ~95% (HPLC); Hypericin, primary pharmaceutical reference standard; Q-100618; SR-05000002344-2; BRD-K29673530-001-03-9; 4,4',5,5',7,7'-Hexahydroxy-2,2'-dimethylnaphthodianthrone; 3,4,6,7,13,14-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-1,8-dione; 3,4,7,8,13,14-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-1,6-dione; 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; Phenanthro[1,9,8-opqra]perylene-7,14-dione,1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-, stereoisomer
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Species Origin Hypericum perforatum ...     Click to Show/Hide
Hypericum perforatum
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Malpighiales
Family: Hypericaceae
Genus: Hypericum
Species: Hypericum perforatum
Disease Human immunodeficiency virus disease [ICD-11: 1C62] Phase 1 [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -6.308
 
MDCK Permeability
 -5.017
 
PAMPA
 - - -
 
HIA
 - - -
 
Distribution
VDss
 -0.438
 
PPB
 96.5%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 ++
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 -
CYP2C9 substrate
 ++
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 +++
CYP3A4 inhibitor
 - -
CYP3A4 substrate
 ++
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 - - -
 
Excretion
CLplasma
 0.213
 
T1/2
 2.556
Toxicity
DILI
 +++
 
Rat Oral Acute Toxicity
 -
 
FDAMDD
 +++
 
Respiratory
 +++
 
Human Hepatotoxicity
 ++
 
Ototoxicity
 +
 
Drug-induced Nephrotoxicity
 +++
 
Drug-induced Neurotoxicity
 ++
 
Hematotoxicity
 +++
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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Formula
C30H16O8
PubChem CID
3663
Canonical SMILES
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
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
InChIKey
YDOIFHVUBCIUHF-UHFFFAOYSA-N
CAS Number
CAS 548-04-9
Herb ID
HBIN029828
SymMap ID
SMIT04377
TCMSP ID
MOL002067
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          N-acetylcysteine      Liver disease     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Increase Mature biofilm disruption
                    In-vitro Model Staphylococcus aureus Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 HYP-PDI in combination with AC had significant ability to eradicate the pre-formed mature biofilms of S. aureus strains.
Target and Pathway
Target(s) COPII-associated small GTPase (SAR1A)  Molecule Info  [3]
References
Reference 1 ClinicalTrials.gov (NCT00000792) A Pharmacologically Guided Phase I/II Study of Daily Orally Administered Synthetic Hypericin in HIV-Infected Subjects
Reference 2 Phototoxic effect of hypericin alone and in combination with acetylcysteine on Staphylococcus aureus biofilms. Photodiagnosis Photodyn Ther. 2015 Jun;12(2):186-92.
Reference 3 Hypericin enhances Beta-lactam antibiotics activity by inhibiting sarA expression in methicillin-resistant Staphylococcus aureus. Acta Pharm Sin B. 2019 Nov;9(6):1174-1182.
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