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Luteolin 6-C-glucopyranosyl-7-O-glucopyranoside

Family: Plantae - Commelinaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavanol Glycoside

Canonical Smiles	OCC1OC(Oc2cc3OC(CC(=O)c3c(c2C2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O)c2ccc(c(c2)O)O)C(C(C1O)O)O
InChI	InChI=1S/C27H32O16/c28-6-15-19(33)22(36)24(38)26(41-15)18-14(42-27-25(39)23(37)20(34)16(7-29)43-27)5-13-17(21(18)35)11(32)4-12(40-13)8-1-2-9(30)10(31)3-8/h1-3,5,12,15-16,19-20,22-31,33-39H,4,6-7H2/t12?,15-,16?,19-,20?,22+,23?,24-,25?,26?,27?/m1/s1
InChIKey	RMZXAZHHEJJOLA-WMKKNOLTSA-N
Formula	C₂₇H₃₂O₁₆
HBA	16
HBD	11
MW	612.54
Rotatable Bonds	6
TPSA	276.52
LogP	-2.8
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.52
Exact Mass	612.17
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Callisia fragrans	Commelinaceae	Plantae	428217

Showing of synonyms

El Sohafy S.M, Nassra R.A, et al. (2021). Chemical profiling and biological screening with potential anti-inflammatory activity of Callisia fragrans grown in Egypt. Natural product research, 2021, 35(23), 5521-5524. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C(CC2=O)Oc(c23)cc(c(c3)C4CCCCO4)OC5CCCCO5

Level: 3

Mol. Weight: 612.54 g/mol

SMILES: O=C1CCOc(c12)cc(c(c2)C3CCCCO3)OC4CCCCO4

Level: 2

Mol. Weight: 612.54 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 612.54 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)ccc(c3)C4CCCCO4

Level: 2

Mol. Weight: 612.54 g/mol

SMILES: O=C1CCOc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 612.54 g/mol

SMILES: O=C1CCOc(c12)ccc(c2)C3CCCCO3

Level: 1

Mol. Weight: 612.54 g/mol

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 612.54 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 612.54 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 612.54 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 612.54 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.62
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.68
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 10.13

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.61
Plasma Protein Binding: 7.68
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: 7.45
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.72
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: 5.58
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: -14721.15
Rat (Acute): 2.33
Rat (Chronic Oral): 4.77
Fathead Minnow: 30.55
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: 462.29
Hydration Free Energy: -2.93
Log(D) at pH=7.4: -1.63
Log(P): -2.0
Log S: -3.36
Log(Vapor Pressure): -15.32
Melting Point: 209.65
pKa Acid: 2.43
pKa Basic: 9.75

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9352
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8871
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8657
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8560
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8339
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8319
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8170
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8165
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8154
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8010
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.7965
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7508
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7446
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7310
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7304
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7278
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7256
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7231
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7226
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7202
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7187
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7179
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7122
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7029
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7010
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	4	0.7008

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