Cylindricine B - Compound Card

Cylindricine B

Select a section from the left sidebar

Cylindricine B

Structure
Zoomed Structure
  • Family: Plantae - Gramineae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Prenylated Flavonoid
Canonical Smiles CC(=CCc1cc(cc(c1O)O)C1CC(=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
InChIKey OZHGVUZFUHBVIS-UHFFFAOYSA-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)
-5.8
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
-1.4

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.01
Plasma Protein Binding
64.15
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
10.29
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.12
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
Safe
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
1.13
Rat (Acute)
2.18
Rat (Chronic Oral)
3.09
Fathead Minnow
4.62
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
481.44
Hydration Free Energy
-10.33
Log(D) at pH=7.4
2.74
Log(P)
4.36
Log S
-5.6
Log(Vapor Pressure)
-8.41
Melting Point
196.4
pKa Acid
6.4
pKa Basic
7.14
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9605
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9335
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9322
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9003
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8995
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8926
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8847
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.8800
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8764
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8755
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8672
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8568
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8533
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8473
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8446
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8402
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8395
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8343
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8335
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8313
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.8311
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8280
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8264
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8210
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8201
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8188
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8187
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8163
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8106
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8087
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8075
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8072
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8057
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8032
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8022
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8016
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8005
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.8005
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7998
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.7997
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7945
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7929
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7925
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.7925
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7919
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7916
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7873
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7864
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7859
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7837
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7822
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7809
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7803
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7798
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7787
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7771
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7754
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7751
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7746
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7718
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7715
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7715
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7708
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7704
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7688
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7662
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7657
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.7624
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 4 0.7618
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7608
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7588
Trichosurin Q29147 TRIC_TRIVU Trichosurus vulpecula 3 0.7586
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7586
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7563
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7517
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7510
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7496
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7494
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7477
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7468
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7451
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 4 0.7416
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7408
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7383
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7360
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7351
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7349
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7336
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7335
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7334
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7332
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7331
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7324
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7323
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7321
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7315
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7312
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7311
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7311
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7291
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7282
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7269
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7266
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7264
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7260
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7258
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7251
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7247
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7244
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7242
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 3 0.7237
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7236
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 4 0.7212
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7207
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7206
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7206
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7206
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7203
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7201
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 4 0.7200
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7199
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7195
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7194
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7192
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.7184
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7177
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7158
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7151
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 4 0.7137
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7130
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7129
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7115
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7093
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7092
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7085
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 5 0.7078
D-alanine--D-alanine ligase Q5HEB7 DDL_STAAC Staphylococcus aureus 3 0.7078
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7064
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7054
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7053
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7043
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7040
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7036
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 5 0.7035
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7034
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7017
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7016
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7016
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7013
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7013
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7007
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7003

Download SDF