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548-04-9 molecular structure
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5,7,11,18,22,24-hexahydroxy-13,16-dimethyloctacyclo[13.11.1.1^{2,10}.0^{3,8}.0^{4,25}.0^{19,27}.0^{21,26}.0^{14,28}]octacosa-1(27),2(28),3,5,7,10,12,14,16,18,21,23,25-tridecaene-9,20-dione

ChemBase ID: 105607
Molecular Formular: C30H16O8
Molecular Mass: 504.44324
Monoisotopic Mass: 504.08451747
SMILES and InChIs

SMILES:
Cc1cc(O)c2C(=O)c3c4c(c(O)cc3O)c3c5c(c(O)cc3O)C(=O)c3c(O)cc(C)c6c1c2c4c5c36
Canonical SMILES:
Oc1cc(C)c2c3c1C(=O)c1c(O)cc(c4c1c3c1c3c2c(C)cc(c3C(=O)c2c1c4c(O)cc2O)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/h3-6,31-36H,1-2H3
InChIKey:
BTXNYTINYBABQR-UHFFFAOYSA-N

Cite this record

CBID:105607 http://www.chembase.cn/molecule-105607.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5,7,11,18,22,24-hexahydroxy-13,16-dimethyloctacyclo[13.11.1.1^{2,10}.0^{3,8}.0^{4,25}.0^{19,27}.0^{21,26}.0^{14,28}]octacosa-1(27),2(28),3,5,7,10,12,14,16,18,21,23,25-tridecaene-9,20-dione
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-1,3,5,7,10,12,14(28),15(27),16,18,21,23,25-tridecaene-9,20-dione
IUPAC Traditional name
hypericin
Synonyms
4,4',5,5',7,7'-Hexahydroxy-2,2'-dimethylnaphthodianthrone
Hypericin
HYPERICIN
4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethylnaphthodianthrone
Cyclo werrol
Hypericum red
4,5,7,4′,5′,7′-Hexahydroxy-2,2′-dimethylnaphthodianthrone
Hypericin from Hypericum perforatum
金丝桃素
4,5,7,4′,5′,7′-六羟基-2,2′-二甲基萘并二蒽酮
金丝桃素 来源于贯叶连翘
CAS Number
548-04-9
EC Number
208-941-0
MDL Number
MFCD00016683
Beilstein Number
1917913
Merck Index
144863
PubChem SID
24880333
162092633
PubChem CID
5281051
CHEBI ID
5835
CHEMBL
286494
Chemspider ID
4444511
Unique Ingredient Identifier
7V2F1075HD
Wikipedia Title
Hypericin

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 6.0381193  H Acceptors
H Donor LogD (pH = 5.5) 7.5736475 
LogD (pH = 7.4) 5.7203846  Log P 7.698295 
Molar Refractivity 139.3118 cm3 Polarizability 57.75268 Å3
Polar Surface Area 155.52 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
1 M NaOH: soluble10 mg/mL expand Show data source
DMSO: soluble expand Show data source
ethanol: soluble5 mg/mL (with sonication) expand Show data source
Apperance
black powder expand Show data source
Blue-black solid expand Show data source
Melting Point
ca 320°C dec. expand Show data source
Storage Condition
2-8°C, Desiccate expand Show data source
European Hazard Symbols
X expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
22-43 expand Show data source
Safety Statements
22-36 expand Show data source
36 expand Show data source
36/37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301 expand Show data source
H301-H317 expand Show data source
GHS Precautionary statements
P264-P270-P301+P310-P321-P405-P501A expand Show data source
P280-P301 + P310 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
~95% (HPLC) expand Show data source
>85% expand Show data source
≥85% (HPLC) expand Show data source
98% expand Show data source
Grade
primary reference standard expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C30H16O8 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02193423 external link
From Hypericum perforatum
Purity: >85%
Selective inhibitor of Protein Kinase C.
Sigma Aldrich - 56690 external link
Biochem/physiol Actions
Anthraquinone-derivative within St. John′s wort. Antibacterial effective against Gram-positive and Gram-negative bacteria.
Sigma Aldrich - H9252 external link
Biochem/physiol Actions
Anthraquinone-derivative within St. John′s wort. Antibacterial effective against Gram-positive and Gram-negative bacteria.
Sigma Aldrich - 00190180 external link
Application
Reference standard in the analysis of herbal medicinal products.
General description
Produced by HWI AnalytikExact content can be found on the certificate

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Inhibitor of protein kinase C: Biochem Biophys. Res. Commun., 165, 1207 (1989); Photochem. Photobiol., 82, 720 (2006). Antiviral and antitumour photosensitizer: Photochem. Photobiol., 54, 95 (1991); Curr. Drug Targets, 3, 55 (2002).
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PATENTS

PATENTS

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INTERNET

INTERNET

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