ANPDB

Select a section from the left sidebar

Norlichexanthone

Family: Plantae - Hyacinthaceae
Kingdom: Fungi, Plantae
Class: Xanthone

Canonical Smiles	Oc1cc(C)c2c(c1)oc1c(c2=O)c(O)cc(c1)O
InChI	InChI=1S/C14H10O5/c1-6-2-7(15)4-10-12(6)14(18)13-9(17)3-8(16)5-11(13)19-10/h2-5,15-17H,1H3
InChIKey	AQZHBCDRWFMXIN-UHFFFAOYSA-N
Formula	C₁₄H₁₀O₅
HBA	5
HBD	3
MW	258.23
Rotatable Bonds	0
TPSA	90.9
LogP	2.37
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	19
Formal Charge	0
Fraction CSP3	0.07
Exact Mass	258.05
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspergillus sp	Trichocomaceae	Fungi	5065
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]
Kamel R.A, Abdel-Razek A.S, et al. (2020). Isoshamixanthone: a new pyrano xanthone from endophytic Aspergillus sp. ASCLA and absolute configuration of epiisoshamixanthone. Nat Prod Res,2020,34(8),1080-1090. [View] [PubMed]

Pubchem: 5281657

Cas: 20716-98-7

Gnps: CCMSLIB00004751494

Zinc: ZINC000005765089

Kegg Ligand: C10087

Chebi: 7632

Nmrshiftdb2: 60076490

Metabolights: MTBLC7632

Chembl: CHEMBL466154

Comptox: DTXSID20174777

Bindingdb: 50350423

CPRiL: 70179

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

Level: 0

Mol. Weight: 258.23 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.02
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.810
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.95

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.970
Plasma Protein Binding: 70.69
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: 4.040
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.120
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.860
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.700
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: Toxic
T. Pyriformis: 4.500
Rat (Acute): 2.030
Rat (Chronic Oral): 2.850
Fathead Minnow: 4.380
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 442.640
Hydration Free Energy: -12.430
Log(D) at pH=7.4: 2.590
Log(P): 3.22
Log S: -4.02
Log(Vapor Pressure): -7.97
Melting Point: 322.21
pKa Acid: 6.8
pKa Basic: 6.63

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	0.9269
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9249
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9203
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9197
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.9021
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.9017
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.8973
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.8931
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8846
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.8841
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8762
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8727
Dihydrofolate reductase	O30463	O30463_MYCAV	Mycobacterium avium	4	0.8696
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8658
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8649
Dihydrofolate reductase	P16184	DYR_PNECA	Pneumocystis carinii	4	0.8640
Dihydrofolate reductase	P16184	DYR_PNECA	Pneumocystis carinii	4	0.8622
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8581
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8553
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8547
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	4	0.8539
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8529
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8510
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8482
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8427
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8410
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8406
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.8402
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8383
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8359
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8338
Dihydrofolate reductase	Q83AB2	Q83AB2_COXBU	Coxiella burnetii	4	0.8328
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8326
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.8302
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8289
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8275
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.8213
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8190
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8185
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.8097
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8065
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8046
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.8028
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8020
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8016
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8005
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7972
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7956
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7948
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7937
Putative cytochrome P450	Q70AS3	Q70AS3_STRPE	Streptomyces peucetius	4	0.7913
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.7911
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7910
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7884
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7881
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7864
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7863
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7836
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7821
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7756
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7740
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	4	0.7723
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7719
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7716
Catalase-peroxidase	Q3JNW6	KATG_BURP1	Burkholderia pseudomallei	3	0.7702
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7687
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7671
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	4	0.7662
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7656
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7642
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	3	0.7639
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7622
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7619
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7589
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7583
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7582
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7577
Cyclin-dependent kinase 6	Q00534	CDK6_HUMAN	Homo sapiens	3	0.7573
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7532
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7530
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7528
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7519
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7502
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7502
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7495
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7485
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7484
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7481
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7464
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7458
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7442
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7436
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7424
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7419
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7408
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7356
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7345
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7340
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	3	0.7336
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7325
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7304
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7300
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7296
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7292
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7286
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7277
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7261
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7259
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7247
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7245
Dihydrofolate reductase	Q81R22	Q81R22_BACAN	Bacillus anthracis	4	0.7230
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7218
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7217
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial	P08559	ODPA_HUMAN	Homo sapiens	3	0.7214
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7185
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7167
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7166
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7159
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	4	0.7123
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7122
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7082
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7073
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7067
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7063
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7061
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	3	0.7059
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7052
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7048
Orotidine 5'-phosphate decarboxylase	O58462	PYRF_PYRHO	Pyrococcus horikoshii	3	0.7044
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7042
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7038
Cytochrome P450	I6YD01	I6YD01_MYCTU	Mycobacterium tuberculosis	4	0.7037
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7035
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7027
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7021
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7006

Download SDF