1,3-dihydroxy-7-methoxy-2(3-methylbut-2enyl) xanthone - Compound Card

1,3-dihydroxy-7-methoxy-2(3-methylbut-2enyl) xanthone

Select a section from the left sidebar

1,3-dihydroxy-7-methoxy-2(3-methylbut-2enyl) xanthone

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1ccc2c(c1)c(=O)c1c(o2)cc(c(c1O)CC=C(C)C)O
InChI InChI=1S/C19H18O5/c1-10(2)4-6-12-14(20)9-16-17(18(12)21)19(22)13-8-11(23-3)5-7-15(13)24-16/h4-5,7-9,20-21H,6H2,1-3H3
InChIKey PBHZGGZVVYPZKJ-UHFFFAOYSA-N
Formula C19H18O5
HBA 5
HBD 2
MW 326.35
Rotatable Bonds 3
TPSA 79.9
LogP 3.87
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 326.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Allanblackia monticola Guttiferae Plantae 1508190

Showing of synonyms

  • Menasria F, Azebaze AG, et al. (2008). Apoptotic effects on B-cell chronic lymphocytic leukemia (B-CLL) cells of heterocyclic compounds isolated from Guttiferaes.. Leukemia research,2008, 32(12), 1914-1926. [View] [PubMed]
Pubchem: 44465828

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 326.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.610
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.130
Plasma Protein Binding
65.2
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
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.870
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.470
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.710
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.050
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
3.890
Rat (Acute)
2.070
Rat (Chronic Oral)
2.630
Fathead Minnow
5.170
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
450.480
Hydration Free Energy
-12.220
Log(D) at pH=7.4
3.260
Log(P)
5.45
Log S
-5.43
Log(Vapor Pressure)
-8.19
Melting Point
169.52
pKa Acid
7.26
pKa Basic
6.94
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9222
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9164
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9128
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.9023
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8853
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8851
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8835
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8805
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8787
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8787
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8695
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8613
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8597
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8591
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.8519
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8510
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8393
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8383
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8255
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8248
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8168
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.8154
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8142
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8079
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8064
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8030
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8008
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7976
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7960
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7952
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7947
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7920
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7906
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7896
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7877
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7871
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7861
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7859
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7850
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7813
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7812
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7788
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7773
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7757
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7755
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7747
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7740
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7677
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7673
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7667
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7612
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7605
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7590
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7584
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7562
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7549
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7549
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7528
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7521
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7515
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7502
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7488
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7481
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7470
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 4 0.7466
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7460
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7437
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7427
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7427
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7416
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7395
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7384
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7377
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7373
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7372
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7369
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7366
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7350
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7339
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7318
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7303
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7298
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7298
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7293
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7291
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7276
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7275
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7271
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7255
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7252
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7248
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7244
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7239
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7220
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7205
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7201
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7193
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7191
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7188
Geranyl diphosphate 2-C-methyltransferase D3KYU3 GPPMT_STRLS Streptomyces lasalocidi 3 0.7188
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7177
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7173
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7171
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7170
A-type flavoprotein Q86QZ1 Q86QZ1_GIAIN Giardia intestinalis 4 0.7165
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7163
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7162
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7159
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7148
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7147
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7143
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7131
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7126
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7123
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7123
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7122
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7119
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7115
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7110
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7103
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7091
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7087
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7087
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7086
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7073
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7069
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7067
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7066
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7059
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7052
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7049
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7048
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7041
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7031
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7022
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7012
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7007
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7001

Download SDF