Apigenin-7-O-beta-D-glucopyranosyl-8-C-beta-D-glucopyranoside - Compound Card

Apigenin-7-O-beta-D-glucopyranosyl-8-C-beta-D-glucopyranoside

Select a section from the left sidebar

Apigenin-7-O-beta-D-glucopyranosyl-8-C-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Caryophyllaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone C-Glycoside
Canonical Smiles OC[C@H]1O[C@@H]([C@H]([C@H]([C@H]1O)O)O)c1c(O[C@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)cc(c2c1oc(cc2=O)c1ccc(cc1)O)O
InChI InChI=1S/C27H30O15/c28-7-15-19(33)21(35)23(37)26(40-15)18-14(41-27-24(38)22(36)20(34)16(8-29)42-27)6-12(32)17-11(31)5-13(39-25(17)18)9-1-3-10(30)4-2-9/h1-6,15-16,19-24,26-30,32-38H,7-8H2/t15-,16-,19+,20-,21+,22+,23+,24-,26-,27+/m1/s1
InChIKey HHRPSKAYQPDDGQ-UMENRPPKSA-N
Formula C27H30O15
HBA 15
HBD 10
MW 594.52
Rotatable Bonds 6
TPSA 260.2
LogP -2.44
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 594.16
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Vaccaria pyramidata Caryophyllaceae Plantae 39387

Showing of synonyms

  • Said R, Hamed A, et al. (2019). Flavone C-glycosides from Vaccaria pyramidata: Structure elucidation by spectroscopy and theoretical calculations. Phytochemistry Letters, 2019, 29, 119-124. [View]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)c(C4CCCCO4)c(cc3)OC5CCCCO5

Level: 3

Mol. Weight: 594.52 g/mol

Structure

SMILES: O=c1ccoc(c12)c(C3CCCCO3)c(cc2)OC4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

Structure

SMILES: O1CCCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4

Level: 2

Mol. Weight: 594.52 g/mol

Structure

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 594.52 g/mol

Structure

SMILES: O=c1ccoc(c12)c(ccc2)C3CCCCO3

Level: 1

Mol. Weight: 594.52 g/mol

Structure

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

Level: 1

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 594.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 594.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.5
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.740
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
7.51

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.720
Plasma Protein Binding
65.7
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
7.070
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-3.880
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.790
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.650
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
-10047.340
Rat (Acute)
2.570
Rat (Chronic Oral)
4.720
Fathead Minnow
20.790
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
548.610
Hydration Free Energy
-3.080
Log(D) at pH=7.4
-0.760
Log(P)
-1.23
Log S
-3.51
Log(Vapor Pressure)
-13.22
Melting Point
204.8
pKa Acid
2.75
pKa Basic
8.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9294
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9218
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8921
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8574
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8547
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8533
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8307
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8051
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8010
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7824
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7614
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7497
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7485
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7473
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7393
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7361
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7315
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7285
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7238
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7224
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7200
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7194
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7181
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 4 0.7175
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7132
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7037
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7026
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7009
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7004

Download SDF