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Forbexanthone

Family: Plantae - Clusiaceae-Guttiferae
Kingdom: Plantae
Class: Xanthone

Canonical Smiles	COc1cc(O)c2c(c1)oc1c(c2=O)cc2c(c1O)OC(C=C2)(C)C
InChI	InChI=1S/C19H16O6/c1-19(2)5-4-9-6-11-15(21)14-12(20)7-10(23-3)8-13(14)24-18(11)16(22)17(9)25-19/h4-8,20,22H,1-3H3
InChIKey	FDTSMQAHJQWMRR-UHFFFAOYSA-N
Formula	C₁₉H₁₆O₆
HBA	6
HBD	2
MW	340.33
Rotatable Bonds	1
TPSA	89.13
LogP	3.55
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.21
Exact Mass	340.09
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Garcinia edulis	Clusiaceae-Guttiferae	Plantae	58227

Showing of synonyms

Magadula JJ. (2010). A bioactive isoprenylated xanthone and other constituents of Garcinia edulis. Fitoterapia,2010,81(5),420-423. [View] [PubMed]

Pubchem: 49775753

Cas: 150527-30-3

Zinc: ZINC000015217368

Nmrshiftdb2: 70022058

No compound-protein relationship available.

SMILES: O1CC=Cc(c2)c1cc(c23)oc4c(c3=O)cccc4

Level: 0

Mol. Weight: 340.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.53
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.690
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.13

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.400
Plasma Protein Binding: 64.32
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: 4.410
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.600
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.630
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.550
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: Safe
T. Pyriformis: 2.650
Rat (Acute): 2.440
Rat (Chronic Oral): 2.470
Fathead Minnow: 4.990
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: 460.170
Hydration Free Energy: -10.640
Log(D) at pH=7.4: 3.060
Log(P): 4.12
Log S: -5.32
Log(Vapor Pressure): -8.06
Melting Point: 231.84
pKa Acid: 7.47
pKa Basic: 4.23

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9334
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9334
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9307
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9307
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9209
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9209
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.9166
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.9166
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9090
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9090
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9041
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9041
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9033
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9033
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.8605
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.8605
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8522
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8522
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8492
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8492
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8376
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8376
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8226
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8226
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8182
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8182
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8159
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8159
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8097
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8097
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7991
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7991
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7984
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7984
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7981
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7981
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7980
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7980
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7970
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7970
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7925
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7925
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7899
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7899
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7851
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7851
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7793
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7793
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7791
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7791
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7774
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7774
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7746
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7746
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7746
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7746
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7687
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7687
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7582
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7582
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7579
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7579
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7557
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7557
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7510
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7510
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7503
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7503
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7457
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7457
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7440
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7440
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7438
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7438
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7406
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7406
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7339
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7339
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7305
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7305
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7300
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7300
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	3	0.7296
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	3	0.7296
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7279
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7279
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7256
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7256
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7251
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7251
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7217
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7217
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7210
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7210
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7207
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7207
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7086
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7086
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7066
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7066
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7044
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7044
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7044
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7044
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7034
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7034
Maltokinase	A1TH50	MAK_MYCVP	Mycolicibacterium vanbaalenii	3	0.7021
Maltokinase	A1TH50	MAK_MYCVP	Mycolicibacterium vanbaalenii	3	0.7021
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7015
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7015
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7006
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7006

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