Cylindricine A - Compound Card

Cylindricine A

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Cylindricine A

Structure
Zoomed Structure
  • Family: Plantae - Gramineae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Prenylated Flavonoid
Canonical Smiles CC(=CCc1cc(cc(c1O)O)[C@@H]1CC(=O)c2c(O1)c(C)c(cc2O)O)C
InChI InChI=1S/C21H22O6/c1-10(2)4-5-12-6-13(7-17(25)20(12)26)18-9-16(24)19-15(23)8-14(22)11(3)21(19)27-18/h4,6-8,18,22-23,25-26H,5,9H2,1-3H3/t18-/m0/s1
InChIKey OZHGVUZFUHBVIS-SFHVURJKSA-N
Formula C21H22O6
HBA 6
HBD 4
MW 370.4
Rotatable Bonds 3
TPSA 107.22
LogP 4.03
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 370.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Imperata cylindrica Gramineae Plantae 80369

Showing of synonyms

  • Nago RDT, Nayim P, et al. (2021). Prenylated Flavonoids and C-15 Isoprenoid Analogues with Antibacterial Properties from the Whole Plant of Imperata cylindrica (L.) Raeusch (Gramineae). Molecules. 2021, 26(16), 4717. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 370.4 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 370.4 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 370.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.81
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.01
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.01
Plasma Protein Binding
83.65
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
10.3
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.08
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.79
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.15
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
0.11
Rat (Acute)
2.18
Rat (Chronic Oral)
3.09
Fathead Minnow
4.56
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
482.46
Hydration Free Energy
-10.32
Log(D) at pH=7.4
2.65
Log(P)
4.33
Log S
-5.64
Log(Vapor Pressure)
-8.54
Melting Point
200.84
pKa Acid
6.4
pKa Basic
7.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9599
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9493
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8996
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8867
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8827
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.8795
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8738
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8732
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8644
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8619
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8594
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8591
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8560
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8543
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8526
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8487
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8476
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8470
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8424
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8423
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8337
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8337
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8312
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.8295
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8275
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8199
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8197
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8169
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8157
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8155
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8129
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8101
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.8063
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8062
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8046
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8040
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.8027
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8015
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.8006
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8001
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7978
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7970
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7966
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7954
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7953
Trichosurin Q29147 TRIC_TRIVU Trichosurus vulpecula 3 0.7944
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7941
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7935
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7928
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7927
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7917
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7866
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7865
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7861
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7858
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7833
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7824
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7821
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7803
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7795
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7793
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7793
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7788
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7771
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7733
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7729
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7717
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7710
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7683
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7672
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7669
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7662
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7653
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7647
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7636
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7632
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7625
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7622
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.7621
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7617
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7613
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7609
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7605
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7602
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7586
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7570
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7555
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7545
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7541
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7536
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7527
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7520
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7514
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7486
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7443
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7437
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7423
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7397
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7387
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7371
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7363
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7357
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7355
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7355
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7351
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7336
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7333
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7318
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7304
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7302
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7299
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7295
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7294
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7291
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7290
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 3 0.7258
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7257
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7257
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7239
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7235
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7234
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7231
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7230
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7223
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 2 0.7223
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7221
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7196
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7186
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7176
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7171
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7168
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7167
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7160
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7137
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7131
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7128
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 4 0.7115
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7103
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7101
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7101
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7097
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7087
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7071
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein Q5SHN1 Q5SHN1_THET8 Thermus thermophilus 3 0.7065
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7064
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7063
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7058
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7056
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7054
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7053
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7024
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7011
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7001
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7001

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