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Cylindraucine

Family: Plantae - Gramineae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Prenylated Flavonoid

Canonical Smiles	COc1c(O)ccc(c1CC=C(C)C)/C=C\1/Oc2c(C1=O)c(O)cc(c2)OC
InChI	InChI=1S/C22H22O6/c1-12(2)5-7-15-13(6-8-16(23)22(15)27-4)9-19-21(25)20-17(24)10-14(26-3)11-18(20)28-19/h5-6,8-11,23-24H,7H2,1-4H3/b19-9+
InChIKey	SNIAZFNYJWSDHH-DJKKODMXSA-N
Formula	C₂₂H₂₂O₆
HBA	6
HBD	2
MW	382.41
Rotatable Bonds	5
TPSA	85.22
LogP	4.24
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.23
Exact Mass	382.14
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.

SMILES: c1ccccc1C=C(C2=O)Oc(c23)cccc3

Level: 1

Mol. Weight: 382.41 g/mol

SMILES: O=C1C(=C)Oc(c12)cccc2

Level: 0

Mol. Weight: 382.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 382.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.64
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.710
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.96

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.280
Plasma Protein Binding: 66.04
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.480
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.050
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.860
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.280
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -4.980
Rat (Acute): 2.140
Rat (Chronic Oral): 2.790
Fathead Minnow: 5.410
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 459.670
Hydration Free Energy: -6.820
Log(D) at pH=7.4: 3.630
Log(P): 4.56
Log S: -6.34
Log(Vapor Pressure): -7.97
Melting Point: 165.77
pKa Acid: 7.69
pKa Basic: 4.73

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9456
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.9314
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9302
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9298
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.9218
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9097
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.9052
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9029
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8973
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8953
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8889
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8826
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8748
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8738
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8569
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8458
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8367
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8304
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8265
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.8219
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.8202
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8172
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8112
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.8090
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8007
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7990
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	3	0.7987
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7983
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7975
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7967
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7911
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7812
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7770
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7732
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7715
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7631
GTPase KRas	P01116	RASK_HUMAN	Homo sapiens	3	0.7629
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7619
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7604
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7536
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7516
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7513
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7447
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7421
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7389
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7387
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7385
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7384
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7375
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7358
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7355
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7344
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7327
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7321
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7296
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	4	0.7280
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7276
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7261
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7228
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7223
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7195
Uridine phosphorylase	P12758	UDP_ECOLI	Escherichia coli	3	0.7194
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7184
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7172
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7159
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7156
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7155
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7155
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7146
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7145
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.7144
Isoflavone-7-O-methyltransferase 8	O24529	7OMT8_MEDSA	Medicago sativa	5	0.7136
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7133
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7121
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7113
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7110
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7107
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7095
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial	Q6NVY1	HIBCH_HUMAN	Homo sapiens	3	0.7093
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7067
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7065
orotidine-5'-phosphate decarboxylase	Q8T6J6	Q8T6J6_PLAFA	Plasmodium falciparum	4	0.7046
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7044
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7030
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7023
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7013
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7001

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