ANPDB

Select a section from the left sidebar

1-hydroxy-2-hydroxymethylanthraquinone 3-glucoside

Family: Plantae - Rubiaceae
Kingdom: Plantae
Class: Anthraquinone
- Subclass: Anthraquinone Glycoside

Canonical Smiles	OC[C@@H]1OC(Oc2cc3C(=O)c4cccc(c4C(=O)c3c(c2CO)O)O)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C21H20O11/c22-5-9-11(31-21-20(30)19(29)17(27)12(6-23)32-21)4-8-14(16(9)26)18(28)13-7(15(8)25)2-1-3-10(13)24/h1-4,12,17,19-24,26-27,29-30H,5-6H2/t12-,17-,19+,20-,21?/m0/s1
InChIKey	ISPHTNSWLQAEID-HGMLGMJCSA-N
Formula	C₂₁H₂₀O₁₁
HBA	11
HBD	7
MW	448.38
Rotatable Bonds	4
TPSA	194.21
LogP	-1.46
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	448.1
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rubia tinctorum	Rubiaceae	Plantae	29802

Showing of synonyms

Herzberg G, Druel T, et al. (1998). Three hydroxymethylanthraquinone glycosides from rubia tinctorum. Phytochemistry,1998,49(1),277–279. [View]

No compound-protein relationship available.

SMILES: c1cccc(C2=O)c1C(=O)c(c23)ccc(c3)OC4CCCCO4

Level: 1

Mol. Weight: 448.38 g/mol

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 448.38 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.68
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.46
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.36

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.77
Plasma Protein Binding: 73.59
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: 9.55
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.56
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.79
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.99
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: -73.2
Rat (Acute): 2.63
Rat (Chronic Oral): 4.59
Fathead Minnow: 3.96
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 604.41
Hydration Free Energy: -5.01
Log(D) at pH=7.4: -0.38
Log(P): 0.85
Log S: -3.07
Log(Vapor Pressure): -12.99
Melting Point: 193.78
pKa Acid: 3.17
pKa Basic: 7.24

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.9317
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9203
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.9063
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8766
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8477
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8472
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8436
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.8398
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8368
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8345
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7974
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7972
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7927
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7831
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7784
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7736
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7674
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7621
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7553
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7540
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7525
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7411
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7309
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7289
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7260
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7252
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7205
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7181
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7178
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7152
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7138
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7123
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7102
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7099
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7032

Download SDF