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Gancaonin G

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone

Canonical Smiles	COc1cc2occ(c(=O)c2c(c1CC=C(C)C)O)c1ccc(cc1)O
InChI	InChI=1S/C21H20O5/c1-12(2)4-9-15-17(25-3)10-18-19(20(15)23)21(24)16(11-26-18)13-5-7-14(22)8-6-13/h4-8,10-11,22-23H,9H2,1-3H3
InChIKey	WLPHLDLTTPUDSI-UHFFFAOYSA-N
Formula	C₂₁H₂₀O₅
HBA	5
HBD	2
MW	352.39
Rotatable Bonds	4
TPSA	79.9
LogP	4.39
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	352.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ficus thonningii	Moraceae	Plantae	309310

Showing of synonyms

Fongang Y, Bankeu J, et al. (2015). Flavonoids and other bioactive constituents from Ficus thonningii Blume (Moraceae). Phytochemistry Letters, 2015, 11, 139-145. [View]

Pubchem: 480780

Cas: 126716-34-5

Zinc: ZINC000005854502

Chebi: 175513

Nmrshiftdb2: 70016939

Chembl: CHEMBL494253

Comptox: DTXSID70155273

No compound-protein relationship available.

SMILES: c1cccc(c12)occ(c2=O)-c3ccccc3

Level: 1

Mol. Weight: 352.39 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 352.39 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 352.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.73
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.750
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.9

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.270
Plasma Protein Binding: 84.55
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: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 3.550
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.040
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.220
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.680
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Toxic
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 1.010
Rat (Acute): 2.220
Rat (Chronic Oral): 2.590
Fathead Minnow: 5.280
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: 465.720
Hydration Free Energy: -11.000
Log(D) at pH=7.4: 3.890
Log(P): 5.16
Log S: -6.55
Log(Vapor Pressure): -8.51
Melting Point: 189.25
pKa Acid: 7.97
pKa Basic: 6.25

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9727
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.9630
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9498
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.9292
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	5	0.9278
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.9101
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.9028
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8962
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.8952
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8853
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8610
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8567
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8532
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8417
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8408
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.8345
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8301
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8301
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8249
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8172
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8125
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8116
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8107
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.8104
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.8083
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8069
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.8064
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8063
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8045
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.8021
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7984
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7984
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7979
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7978
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7940
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7936
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7923
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7904
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7895
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.7875
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7863
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7854
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7853
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7828
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7805
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7795
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7756
Poly [ADP-ribose] polymerase tankyrase-1	O95271	TNKS1_HUMAN	Homo sapiens	4	0.7750
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7735
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7730
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7729
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7696
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7690
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7687
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7673
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	2	0.7658
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7653
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7648
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7645
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7625
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7609
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7585
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7584
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7554
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7547
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7534
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7524
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7521
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7506
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7497
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7497
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7463
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7463
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7459
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7432
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7425
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7408
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7403
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7380
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7380
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7378
Isoflavone-7-O-methyltransferase 8	O24529	7OMT8_MEDSA	Medicago sativa	5	0.7374
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7362
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7356
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7346
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7339
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7338
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7336
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7315
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7315
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7309
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7301
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7291
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7289
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7285
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7278
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.7249
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7248
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7244
Renin	P00797	RENI_HUMAN	Homo sapiens	2	0.7232
Ribonuclease TTHA0252	Q5SLP1	RNSE_THET8	Thermus thermophilus	3	0.7218
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7212
NmrA-like family domain-containing protein 1	Q9HBL8	NMRL1_HUMAN	Homo sapiens	2	0.7203
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7197
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7196
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7187
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7179
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7171
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7169
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7164
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7162
Ketimine reductase mu-crystallin	O54983	CRYM_MOUSE	Mus musculus	2	0.7155
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7153
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7151
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7147
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7118
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7113
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7095
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7094
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7094
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7070
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7054
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	3	0.7053
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7051
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7048
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7042
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7040
NTPase P4	Q94M05	Q94M05_9VIRU	Pseudomonas phage phi12	2	0.7034
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7026
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7020
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7017
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7015
Myosin heavy chain, striated muscle	P24733	MYS_ARGIR	Argopecten irradians	3	0.7007
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7004
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7004
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7000

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