Haronginanthrone - Compound Card

Haronginanthrone

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Haronginanthrone

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles CCCc1cc(O)cc2c1C(=O)c1c(C2=O)cccc1O
InChI InChI=1S/C17H14O4/c1-2-4-9-7-10(18)8-12-14(9)17(21)15-11(16(12)20)5-3-6-13(15)19/h3,5-8,18-19H,2,4H2,1H3
InChIKey HBNFWKSLJKIOTM-UHFFFAOYSA-N
Formula C17H14O4
HBA 4
HBD 2
MW 282.29
Rotatable Bonds 2
TPSA 74.6
LogP 2.83
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 282.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Psorospermum aurantiacum Hypericaceae Plantae 999533

Showing of synonyms

  • Tiani G, Ahmed I, et al. (2013). Kenganthranol F, a new Anthranol from Psorospermum aurantiacum.. Natural Product Communications, 2013, 8(1), 103-104. [View] [PubMed]
Pubchem: 21778867
Nmrshiftdb2: 70095209

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 282.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.55
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.92
Plasma Protein Binding
62.12
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.11
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.47
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.91
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.29
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Toxic
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
5.03
Rat (Acute)
2.5
Rat (Chronic Oral)
2.79
Fathead Minnow
4.36
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
421.27
Hydration Free Energy
-8.29
Log(D) at pH=7.4
2.82
Log(P)
4.57
Log S
-5.91
Log(Vapor Pressure)
-7.98
Melting Point
193.31
pKa Acid
6.92
pKa Basic
6.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9458
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9131
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8934
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8931
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8890
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8849
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8713
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8710
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8690
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8645
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8577
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8562
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8440
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8406
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.8369
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8329
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8308
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8287
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8272
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8264
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8190
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.8175
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8169
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.8084
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8084
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.8069
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8069
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8065
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8063
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8052
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8050
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8044
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8035
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8035
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8015
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7932
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7896
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7873
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7867
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7826
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7826
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7822
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7792
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7754
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7749
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7710
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7687
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7607
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7594
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7563
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7557
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7551
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7491
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7491
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7488
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7474
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7465
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7465
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7458
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7431
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7396
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7350
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7308
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7306
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7296
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7289
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7271
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7242
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7240
Heat shock protein 83 P12861 HSP83_TRYBB Trypanosoma brucei brucei 3 0.7233
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7213
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7209
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7197
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7192
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7186
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7179
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7173
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7167
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7136
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7133
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7131
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7124
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7108
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7107
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7082
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 3 0.7079
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7059
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7054
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7045
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7040
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7036
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7034
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7025
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7019
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7014

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