Griseoxanthone C - Compound Card

Griseoxanthone C

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Griseoxanthone C

Structure
Zoomed Structure
  • Family: Plantae - Hyacinthaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1cc(O)c2c(c1)oc1c(c2=O)c(C)cc(c1)O
InChI InChI=1S/C15H12O5/c1-7-3-8(16)4-11-13(7)15(18)14-10(17)5-9(19-2)6-12(14)20-11/h3-6,16-17H,1-2H3
InChIKey UIKVQKMDLQHSKA-UHFFFAOYSA-N
Formula C15H12O5
HBA 5
HBD 2
MW 272.26
Rotatable Bonds 1
TPSA 79.9
LogP 2.67
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 272.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dacryodes edulis Burseraceae Plantae 246365
2 Ledebouria graminifolia Hyacinthaceae Plantae 2826844

Showing of synonyms

  • Mutanyatta J, Matapa BG, et al. (2003). Homoisoflavonoids and xanthones from the tubers of wild and in vitro regenerated Ledebouria graminifolia and cytotoxic activities of some of the homoisoflavonoids. Phytochemistry, 2003, 62(5), 797–804. [View]
  • Dongmo KJJ, Tali MBT, et al. (2023). In vitro antiplasmodial activity and toxicological profile of extracts, fractions and chemical constituents of leaves and stem bark from Dacryodes edulis (Burseraceae).. BMC complementary medicine and therapies,2023, 23(1), 211. [View] [PubMed]
Pubchem: 5377910
Chebi: 181512
Nmrshiftdb2: 80011866
CPRiL: 421152
Structure

SMILES: c1cccc(c12)oc3c(c2=O)cccc3

Level: 0

Mol. Weight: 272.26 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.580
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.370
Plasma Protein Binding
71.63
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
Non-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
2.370
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.270
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.590
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.260
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.600
Rat (Acute)
2.020
Rat (Chronic Oral)
2.560
Fathead Minnow
4.710
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
424.500
Hydration Free Energy
-10.570
Log(D) at pH=7.4
2.820
Log(P)
3.51
Log S
-4.83
Log(Vapor Pressure)
-7.25
Melting Point
270.53
pKa Acid
8.54
pKa Basic
4.93
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9397
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.9351
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9271
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9256
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.9245
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9232
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9217
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.9152
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8921
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8889
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8812
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8766
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8749
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.8742
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8733
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8696
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8659
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8571
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8569
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8558
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8532
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8520
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8490
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8466
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.8458
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8445
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8408
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8408
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8399
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8375
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8361
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8354
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8349
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8340
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8308
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8300
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8258
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8224
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8195
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8161
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8109
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8082
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8072
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8012
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8012
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7979
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7976
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7971
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7970
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7947
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7936
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7921
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7893
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7884
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7882
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7846
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7831
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7826
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 3 0.7818
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7793
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7780
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7767
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7715
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7711
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7690
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7685
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7680
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7669
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7658
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7655
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7648
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7622
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7601
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7593
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7580
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7579
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7574
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7556
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7534
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7529
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7527
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7510
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7500
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7499
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7481
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7475
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7473
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7452
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7451
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7410
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7409
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7399
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7388
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7388
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7351
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7351
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7343
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7336
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7325
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 3 0.7313
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7312
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7301
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial P08559 ODPA_HUMAN Homo sapiens 3 0.7300
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7297
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7295
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7294
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7291
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7287
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7279
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7262
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7261
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 3 0.7256
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7251
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7248
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7239
Ribosomal RNA small subunit methyltransferase E Q5SKI6 Q5SKI6_THET8 Thermus thermophilus 4 0.7234
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 2 0.7234
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 3 0.7217
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7209
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7201
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7199
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7188
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7173
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7165
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7155
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7155
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7149
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7149
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7142
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7127
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7121
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7092
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7083
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7081
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 4 0.7068
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7068
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7065
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7058
Cytochrome P450 I6YD01 I6YD01_MYCTU Mycobacterium tuberculosis 4 0.7051
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7043
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7042
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7038
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7021
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7015
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7008

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