Cirsimaritin 4'-glucoside - Compound Card

Cirsimaritin 4'-glucoside

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Cirsimaritin 4'-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside
Canonical Smiles OC[C@H]1O[C@@H](Oc2ccc(cc2)c2cc(=O)c3c(o2)cc(c(c3O)OC)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C23H24O11/c1-30-15-8-14-17(19(27)22(15)31-2)12(25)7-13(33-14)10-3-5-11(6-4-10)32-23-21(29)20(28)18(26)16(9-24)34-23/h3-8,16,18,20-21,23-24,26-29H,9H2,1-2H3/t16-,18-,20+,21-,23-/m1/s1
InChIKey RETJLKUBHXTIGH-FZFRBNDOSA-N
Formula C23H24O11
HBA 11
HBD 5
MW 476.43
Rotatable Bonds 6
TPSA 168.28
LogP 0.36
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 476.13
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Rosmarinuseriocalyx Lamiaceae Plantae

Showing of synonyms

  • Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]
CPRiL: 86537
Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 476.43 g/mol

Structure

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

Level: 1

Mol. Weight: 476.43 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 476.43 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 476.43 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 476.43 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 476.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.61
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.020
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.110
Plasma Protein Binding
88.52
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
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
8.460
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.420
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.920
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.260
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
-223.150
Rat (Acute)
2.450
Rat (Chronic Oral)
3.750
Fathead Minnow
4.210
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
564.720
Hydration Free Energy
-3.410
Log(D) at pH=7.4
1.200
Log(P)
0.48
Log S
-4.23
Log(Vapor Pressure)
-11.97
Melting Point
212.94
pKa Acid
6.47
pKa Basic
4.02
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9782
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9328
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9304
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.9301
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9105
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9002
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8964
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8895
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8881
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8851
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8823
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8781
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8769
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8765
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8636
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8608
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8543
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8528
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8516
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8513
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8469
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8463
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8442
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8427
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.8331
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8321
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8286
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8271
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8175
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8142
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8132
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 3 0.8126
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8100
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8074
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.8062
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.8032
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8030
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8021
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7914
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7912
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7884
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7883
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7868
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7860
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7826
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7823
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7821
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.7817
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7792
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7754
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7749
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7746
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7710
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7675
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7659
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 4 0.7630
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7626
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7623
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7606
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7582
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7578
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7566
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7550
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7546
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7542
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7536
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase, chloroplastic Q9FYS3 HGGL_SECCE Secale cereale 3 0.7532
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7530
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7528
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7525
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7510
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7507
Nucleoside phosphorylase, putative Q57VZ2 Q57VZ2_TRYB2 Trypanosoma brucei brucei 4 0.7491
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7488
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7481
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7470
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7469
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7466
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7466
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7457
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7445
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7418
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7395
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7389
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 4 0.7359
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7345
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7337
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7309
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7301
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7299
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7286
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7274
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7260
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7259
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7258
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7245
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7231
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7226
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7208
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 4 0.7205
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7203
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7198
BMP-2-inducible protein kinase Q9NSY1 BMP2K_HUMAN Homo sapiens 3 0.7192
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7187
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7186
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 4 0.7182
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7182
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7181
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7179
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7175
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7173
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7164
Mitogen-activated protein kinase kinase kinase 7 O43318 M3K7_HUMAN Homo sapiens 4 0.7164
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7117
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7116
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7109
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7108
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7106
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7098
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7098
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7096
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7082
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7081
DNA gyrase subunit B Q839Z1 GYRB_ENTFA Enterococcus faecalis 3 0.7062
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7056
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7046
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7045
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7044
Purine nucleoside phosphorylase 2 P45563 XAPA_ECOLI Escherichia coli 3 0.7037
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7024
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7018
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7015
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7015
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7014
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7006
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7000

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