Hyperixanthone - Compound Card

Hyperixanthone

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Hyperixanthone

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Xanthone
    • Subclass: Xanthone Derivative
Canonical Smiles C=CC(c1c(O)cc(c2c1oc1C=C(O)C(=O)C(c1c2=O)(CC=C(C)C)CC=C(C)C)O)(C)C
InChI InChI=1S/C28H32O6/c1-8-27(6,7)22-18(30)13-17(29)21-24(32)23-20(34-25(21)22)14-19(31)26(33)28(23,11-9-15(2)3)12-10-16(4)5/h8-10,13-14,29-31H,1,11-12H2,2-7H3
InChIKey PJKSIBQLLLINDT-UHFFFAOYSA-N
Formula C28H32O6
HBA 6
HBD 3
MW 464.56
Rotatable Bonds 6
TPSA 107.97
LogP 6.1
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 464.22
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Hypericum riparium Hypericaceae Plantae 269018

Showing of synonyms

  • Tala MF, Talontsi FM, et al. (2015). Antimicrobial and cytotoxic constituents from native Cameroonian medicinal plant Hypericum riparium.. Fitoterapia,2015, 102, 149-155. [View] [PubMed]
Pubchem: 135923532
Chebi: 66056
Metabolights: MTBLC66056

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc3c(c2=O)CC(=O)C=C3

Level: 0

Mol. Weight: 464.56 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.06
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.84
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.11
Plasma Protein Binding
65.48
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.97
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.33
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.54
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.51
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-80.51
Rat (Acute)
2.51
Rat (Chronic Oral)
3.33
Fathead Minnow
5.48
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
495.73
Hydration Free Energy
-3.2
Log(D) at pH=7.4
3.96
Log(P)
7.32
Log S
-6.44
Log(Vapor Pressure)
-9.19
Melting Point
190.34
pKa Acid
8.67
pKa Basic
4.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8762
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.8758
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8726
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8561
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8536
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8010
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7968
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7952
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.7870
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7826
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7816
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7757
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7457
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7422
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7373
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7333
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7246
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7226
Casein kinase I isoform gamma-2 P78368 KC1G2_HUMAN Homo sapiens 4 0.7223
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7222
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7213
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7179
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7164
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7142
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7139
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7113
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7108
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7073
Thymidine phosphorylase P07650 TYPH_ECOLI Escherichia coli 4 0.7069
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7038

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