1,6-dihydroxy-3,7-di-O,O-diprenylxanthone - Compound Card

1,6-dihydroxy-3,7-di-O,O-diprenylxanthone

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1,6-dihydroxy-3,7-di-O,O-diprenylxanthone

Structure
Zoomed Structure
  • Family: Plantae - Clusiaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles CC(=CCOc1cc(O)c2c(c1)oc1c(c2=O)cc(c(c1)O)OCC=C(C)C)C
InChI InChI=1S/C23H24O6/c1-13(2)5-7-27-15-9-18(25)22-21(10-15)29-19-12-17(24)20(11-16(19)23(22)26)28-8-6-14(3)4/h5-6,9-12,24-25H,7-8H2,1-4H3
InChIKey YCOCMTVJTWKNSQ-UHFFFAOYSA-N
Formula C23H24O6
HBA 6
HBD 2
MW 396.44
Rotatable Bonds 6
TPSA 89.13
LogP 5.05
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.26
Exact Mass 396.16
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Garcinia nobilis Clusiaceae Plantae 469933

Showing of synonyms

  • Dzoyem J, Lannang A, et al. (2015). Anti-inflammatory activity of benzophenone and xanthone derivatives isolated from Garcinia (Clusiaceae) species. Phytochemistry Letters, 2015, 14, 153-158. [View]
Pubchem: 132556720

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 396.44 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.74
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.48
Plasma Protein Binding
62.85
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.66
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.14
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.47
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.31
Micronucleos
Toxic
NR-AhR
Toxic
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
-7.84
Rat (Acute)
2.1
Rat (Chronic Oral)
2.45
Fathead Minnow
5.66
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
477.54
Hydration Free Energy
-7.47
Log(D) at pH=7.4
3.57
Log(P)
6.25
Log S
-6.69
Log(Vapor Pressure)
-8.73
Melting Point
190.02
pKa Acid
8.22
pKa Basic
6.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9345
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9211
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9157
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9149
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9046
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9002
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8866
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8849
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8826
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8628
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.8623
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8583
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8543
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8531
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8494
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8475
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8442
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8438
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8402
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8390
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8292
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8291
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8290
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8204
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8189
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8151
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8095
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.8073
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8068
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8049
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8027
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8001
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7974
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7959
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7956
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7933
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7925
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7891
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7878
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7848
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7836
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7829
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7782
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7734
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7706
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7691
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7652
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7636
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7632
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7614
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7599
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7594
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7573
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7570
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7559
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7548
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7548
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7540
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7537
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7531
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7529
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7525
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7520
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7511
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7493
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7475
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7465
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7460
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7431
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7420
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7419
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7419
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7405
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7403
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7402
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7399
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7389
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7383
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7380
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7376
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7358
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7355
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7353
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7330
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7329
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7316
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7283
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7274
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 4 0.7267
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7262
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7245
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7239
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7230
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7225
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7218
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7216
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.7213
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7212
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7211
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7189
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7184
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7183
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7176
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7164
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7163
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7159
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7155
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7143
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7139
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7129
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7123
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7123
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7115
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7087
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7086
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7080
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7077
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7068
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7061
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7055
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7039
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7036
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7034
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7033
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7027
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7020
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7019
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7019

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