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Rhamnetin-3-O-beta-D-galactopyranoside

Family: Plantae - Lamiaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)OC)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@H]1O)O)O
InChI	InChI=1S/C22H22O12/c1-31-9-5-12(26)15-13(6-9)32-20(8-2-3-10(24)11(25)4-8)21(17(15)28)34-22-19(30)18(29)16(27)14(7-23)33-22/h2-6,14,16,18-19,22-27,29-30H,7H2,1H3/t14-,16+,18+,19-,22+/m1/s1
InChIKey	PHEWILLIAJUBQE-UVHBULKNSA-N
Formula	C₂₂H₂₂O₁₂
HBA	12
HBD	7
MW	478.41
Rotatable Bonds	5
TPSA	199.51
LogP	-0.24
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	478.11
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Plectranthus africanus	Lamiaceae	Plantae	2485366

Showing of synonyms

Nzogong RT, Nganou BK, et al. (2018). Three New Abietane-Type Diterpenoids from Plectranthus africanus and Their Antibacterial Activities.. Planta medica,2018, 84(1), 59-64. [View] [PubMed]

Pubchem: 10344991

Cas: 62858-07-5

Zinc: ZINC000038576345

Nmrshiftdb2: 60058168

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 478.41 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 478.41 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 478.41 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 478.41 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 478.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 478.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.45
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.430
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1.36

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.940
Plasma Protein Binding: 79.92
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: 11.760
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.960
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.110
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.300
Micronucleos: Toxic
NR-AhR: Toxic
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: -189.350
Rat (Acute): 2.360
Rat (Chronic Oral): 3.800
Fathead Minnow: 4.140
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 612.410
Hydration Free Energy: -3.680
Log(D) at pH=7.4: 0.500
Log(P): 0.41
Log S: -4.77
Log(Vapor Pressure): -11.3
Melting Point: 192.38
pKa Acid: 5.53
pKa Basic: 6.17

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9739
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9367
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9000
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8941
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8932
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8659
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8534
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8460
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8419
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8348
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8308
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8211
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.8000
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7993
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7945
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7944
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7783
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7773
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	4	0.7771
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7766
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7752
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7724
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7721
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7713
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7593
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7550
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7548
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7528
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7505
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7503
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7483
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7446
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7438
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7436
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7422
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7349
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7348
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7328
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7315
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7304
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7291
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7290
Periplasmic pH-dependent serine endoprotease DegQ	P39099	DEGQ_ECOLI	Escherichia coli	4	0.7277
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7230
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7225
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7214
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7213
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7195
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7174
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7119
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.7099
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7084
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7047
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7022
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7021

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