6-C-glucosyl-8-C-arabinosylapigenin - Compound Card

6-C-glucosyl-8-C-arabinosylapigenin

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6-C-glucosyl-8-C-arabinosylapigenin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside
Canonical Smiles OC[C@H]1OC([C@H]([C@@H]1O)O)c1c(O)c(C2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)c(c2c1oc(cc2=O)c1ccc(cc1)O)O
InChI InChI=1S/C26H28O14/c27-6-12-17(31)21(35)23(37)25(39-12)15-19(33)14-10(30)5-11(8-1-3-9(29)4-2-8)38-24(14)16(20(15)34)26-22(36)18(32)13(7-28)40-26/h1-5,12-13,17-18,21-23,25-29,31-37H,6-7H2/t12-,13-,17-,18-,21+,22+,23-,25?,26?/m1/s1
InChIKey TUIJPUWSXVFWSH-UFXZNCPXSA-N
Formula C26H28O14
HBA 14
HBD 10
MW 564.5
Rotatable Bonds 5
TPSA 250.97
LogP -1.75
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.42
Exact Mass 564.15
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Chrysanthemum macrocarpum Asteraceae Plantae 13422

Showing of synonyms

  • Boutaghane N, Voutquenne-Nazabadioko L, et al. (2013). A new triterpenic diester from the aerial parts of Chrysanthemum macrocarpum. Phytochemistry Letters,2013,6,519-525. [View]
Pubchem: 162864114

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1c(c2)cc(C3CCCO3)c(c24)oc(cc4=O)-c5ccccc5

Level: 3

Mol. Weight: 564.5 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4

Level: 2

Mol. Weight: 564.5 g/mol

Structure

SMILES: O=c1ccoc(c12)c(C3CCCO3)cc(c2)C4CCCCO4

Level: 2

Mol. Weight: 564.5 g/mol

Structure

SMILES: O1CCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4

Level: 2

Mol. Weight: 564.5 g/mol

Structure

SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3

Level: 1

Mol. Weight: 564.5 g/mol

Structure

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

Level: 1

Mol. Weight: 564.5 g/mol

Structure

SMILES: O1CCCC1c(ccc2)c(c23)occc3=O

Level: 1

Mol. Weight: 564.5 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 564.5 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 564.5 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 564.5 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 564.5 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
-6.180
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
5.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.640
Plasma Protein Binding
54.84
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
8.030
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.290
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.750
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.390
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
-4378.780
Rat (Acute)
2.510
Rat (Chronic Oral)
4.870
Fathead Minnow
9.150
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
658.380
Hydration Free Energy
-3.160
Log(D) at pH=7.4
-1.040
Log(P)
-0.03
Log S
-3.46
Log(Vapor Pressure)
-13.09
Melting Point
210.19
pKa Acid
2.27
pKa Basic
10.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8849
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8849
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8709
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8709
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8143
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8143
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8044
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8044
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7853
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7853
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7675
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7675
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7658
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7658
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7613
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7613
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7530
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7530
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7507
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7507
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7445
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7445
Nuclear receptor subfamily 5 group A member 2 O00482 NR5A2_HUMAN Homo sapiens 4 0.7295
Nuclear receptor subfamily 5 group A member 2 O00482 NR5A2_HUMAN Homo sapiens 4 0.7295
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7286
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7286
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.7265
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.7265
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7245
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7245
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7156
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7156
ATP synthase subunit alpha Q9X1U7 ATPA_THEMA Thermotoga maritima 4 0.7128
ATP synthase subunit alpha Q9X1U7 ATPA_THEMA Thermotoga maritima 4 0.7128
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7107
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7107
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7045
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7045
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7042
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7042
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7038
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7038

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