5,7,2',4',5'-pentahydroxyflavone 3-O-beta-D-galactopyranoside - Compound Card

5,7,2',4',5'-pentahydroxyflavone 3-O-beta-D-galactopyranoside

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5,7,2',4',5'-pentahydroxyflavone 3-O-beta-D-galactopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Cistaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2cc(O)c(cc2O)O)[C@@H]([C@H]([C@H]1O)O)O
InChI InChI=1S/C21H20O13/c22-5-13-15(28)17(30)18(31)21(33-13)34-20-16(29)14-11(27)1-6(23)2-12(14)32-19(20)7-3-9(25)10(26)4-8(7)24/h1-4,13,15,17-18,21-28,30-31H,5H2/t13-,15+,17+,18-,21+/m1/s1
InChIKey OXTVMIAIDOBIIV-DTGCRPNFSA-N
Formula C21H20O13
HBA 13
HBD 9
MW 480.38
Rotatable Bonds 4
TPSA 230.74
LogP -0.83
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 480.09
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Helianthemum getulum Cistaceae Plantae 2020754

Showing of synonyms

  • Terfassi S, Dauvergne X, et al. (2022). First report on phytochemical investigation, antioxidant and antidiabetic activities of Helianthemum getulum. Natural product research, 2022, 36(11), 2806-2813. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 480.38 g/mol

Structure

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

Level: 1

Mol. Weight: 480.38 g/mol

Structure

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

Level: 1

Mol. Weight: 480.38 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 480.38 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 480.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 480.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.2
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-6.190
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
3.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.700
Plasma Protein Binding
71.91
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
12.970
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.510
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.170
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.470
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
-156.620
Rat (Acute)
2.430
Rat (Chronic Oral)
4.100
Fathead Minnow
3.470
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
684.430
Hydration Free Energy
-4.280
Log(D) at pH=7.4
-0.530
Log(P)
0.42
Log S
-4.18
Log(Vapor Pressure)
-12.14
Melting Point
204.35
pKa Acid
5.34
pKa Basic
9.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9575
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8891
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8831
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8669
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8530
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8473
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8323
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8270
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8238
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8204
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8189
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8187
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8168
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8165
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8122
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8047
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7900
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7698
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7680
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7675
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7671
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7647
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7555
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7540
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7539
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7539
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7490
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7484
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7475
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7470
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7397
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7386
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7268
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7245
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7199
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7161
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7141
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7133
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7089
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7063
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7038

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