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Phlorizine

Family: Plantae - Rubiaceae
Kingdom: Plantae
Class: Chalcone
- Subclass: Dihydrochalcone

Canonical Smiles	OCC1OC(Oc2cc(O)cc(c2C(=O)CCc2ccc(cc2)O)O)C(C(C1O)O)O
InChI	InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2
InChIKey	IOUVKUPGCMBWBT-UHFFFAOYSA-N
Formula	C₂₁H₂₄O₁₀
HBA	10
HBD	7
MW	436.41
Rotatable Bonds	7
TPSA	177.14
LogP	-0.2
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	436.14
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Galium brunneum	Rubiaceae	Plantae	25168

Showing of synonyms

Smadi A, Bitam F, et al. (2020). Chemical constituents of the aerial parts of Algerian Galium brunneum:Isolation of new hydroperoxy sterol glucosyl derivatives. Phytochemistry Letters, 2020, 38, 39-45. [View]

Pubchem: 4789

Chebi: 182131

Nmrshiftdb2: 70085582

Chembl: CHEMBL45266

Bindingdb: 237198

No compound-protein relationship available.

SMILES: c1ccccc1CCC(=O)c2c(cccc2)OC3CCCCO3

Level: 2

Mol. Weight: 436.41 g/mol

SMILES: c1ccccc1C(=O)CCc2ccccc2

Level: 1

Mol. Weight: 436.41 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 436.41 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 436.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 436.41 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -7.0
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.48
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.8

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.76
Plasma Protein Binding: 10.18
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 13.25
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.79
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.6
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.72
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -32.04
Rat (Acute): 2.31
Rat (Chronic Oral): 3.93
Fathead Minnow: 4.12
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 580.79
Hydration Free Energy: -7.95
Log(D) at pH=7.4: 0.35
Log(P): -0.12
Log S: -3.11
Log(Vapor Pressure): -11.74
Melting Point: 162.63
pKa Acid: 4.89
pKa Basic: 7.35

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9504
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9467
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9386
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.9090
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8998
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8989
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8941
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8869
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8795
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8765
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8755
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8703
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8626
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8615
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.8545
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8527
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8493
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.8480
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8383
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8341
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8316
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.8308
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.8267
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.8243
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8217
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8139
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8098
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.8073
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8063
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8055
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7985
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7963
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7962
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7924
Karilysin	D0EM77	KLY_TANFA	Tannerella forsythia	3	0.7865
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7864
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7835
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7812
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7808
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7805
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7778
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7776
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7745
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	3	0.7743
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7738
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7737
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7733
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7720
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7699
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7692
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7630
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7627
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7593
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7588
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7578
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7554
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7536
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7511
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7508
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7495
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7493
Flavonoid 3-O-glucosyltransferase	A6XNC6	UGFGT_MEDTR	Medicago truncatula	3	0.7452
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7439
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.7438
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7428
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7417
Seed lectin subunit I	P05045	LEC1_VIGUC	Vigna unguiculata subsp. cylindrica	3	0.7410
Transthyretin	P02766	TTHY_HUMAN	Homo sapiens	4	0.7406
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7398
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7392
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7383
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7366
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7363
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7357
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	3	0.7354
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7352
Matrilysin	P09237	MMP7_HUMAN	Homo sapiens	3	0.7285
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7262
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7262
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	4	0.7248
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7248
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7247
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7240
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7240
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7233
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7207
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7204
Cellular tumor antigen p53	P04637	P53_HUMAN	Homo sapiens	3	0.7201
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7187
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7177
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7167
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7152
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7143
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7134
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	3	0.7133
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7129
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7128
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7121
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7117
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7102
Ribonuclease TTHA0252	Q5SLP1	RNSE_THET8	Thermus thermophilus	3	0.7098
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7095
Phenolphthiocerol/phthiocerol polyketide synthase subunit C	P96202	PPSC_MYCTU	Mycobacterium tuberculosis	3	0.7089
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7085
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.7082
6-phosphogluconate dehydrogenase, decarboxylating	P96789	6PGD_LACLM	Lactococcus lactis subsp. cremoris	3	0.7073
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7069
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7046
Cyclic GMP-AMP synthase	Q8C6L5	CGAS_MOUSE	Mus musculus	3	0.7041
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7034
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7030
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7026
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7004
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7004
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7003
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7003

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