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Ciliatin B

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone

Canonical Smiles	COc1cc(ccc1O)c1cc(=O)c2c(o1)cc(c1c2OC(C)(C)CC1)O
InChI	InChI=1S/C21H20O6/c1-21(2)7-6-12-14(23)9-18-19(20(12)27-21)15(24)10-16(26-18)11-4-5-13(22)17(8-11)25-3/h4-5,8-10,22-23H,6-7H2,1-3H3
InChIKey	FZANCCSFDNGROR-UHFFFAOYSA-N
Formula	C₂₁H₂₀O₆
HBA	6
HBD	2
MW	368.39
Rotatable Bonds	2
TPSA	89.13
LogP	3.98
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	368.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Dorstenia ciliata	Moraceae	Plantae	2604984

Showing of synonyms

Ngadjui BT, Ngameni B, et al. (2002). Prenylated and geranylated chalcones and flavones from the aerial parts of Dorstenia ciliata. Bulletin of The Chemical Society of Ethiopia, 2002, 16(2), 157-164. [View]

Pubchem: 44258210

Cas: 539826-42-1

Zinc: ZINC000059734876

No compound-protein relationship available.

SMILES: O1CCCc(c1c23)ccc3oc(cc2=O)-c4ccccc4

Level: 1

Mol. Weight: 368.39 g/mol

SMILES: O1CCCc(c1c23)ccc3occc2=O

Level: 0

Mol. Weight: 368.39 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 368.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.63
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.790
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.97

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.420
Plasma Protein Binding: 88.0
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: 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: 5.780
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.950
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.220
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.170
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: -1.440
Rat (Acute): 2.360
Rat (Chronic Oral): 1.900
Fathead Minnow: 4.870
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: 490.750
Hydration Free Energy: -8.750
Log(D) at pH=7.4: 3.970
Log(P): 4.13
Log S: -6.05
Log(Vapor Pressure): -8.7
Melting Point: 263.45
pKa Acid: 8.48
pKa Basic: 5.19

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9810
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9619
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9550
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9527
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9407
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9391
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9376
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9243
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9166
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9083
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.9071
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9021
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8994
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.8865
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8809
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8702
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8680
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8667
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.8575
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8568
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8563
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.8562
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8532
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8513
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8404
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8390
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8262
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.8255
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8232
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8203
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8159
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8154
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8153
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8135
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8097
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8094
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.8093
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8052
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8027
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7996
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7900
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7868
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7862
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7710
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7677
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7637
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7633
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7627
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7625
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7599
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7568
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7512
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7506
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7454
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7450
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7437
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7434
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7416
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	4	0.7412
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7378
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7374
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7369
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7366
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7362
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7360
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	2	0.7351
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7322
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7316
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	2	0.7304
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7278
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7275
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7271
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7269
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7261
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7254
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7248
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7246
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7239
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7239
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7227
Histone-lysine N-methyltransferase EHMT2	Q96KQ7	EHMT2_HUMAN	Homo sapiens	3	0.7207
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7206
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7199
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7194
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7191
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7190
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7189
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7188
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	3	0.7181
Histone-lysine N-methyltransferase 2A	Q03164	KMT2A_HUMAN	Homo sapiens	3	0.7169
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7155
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7149
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7134
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7132
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7126
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7121
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7119
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7097
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7091
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7062
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7052
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7047
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7031
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7018
Histone-lysine N-methyltransferase 2C	Q8NEZ4	KMT2C_HUMAN	Homo sapiens	3	0.7017
DNA (cytosine-5)-methyltransferase 3A	O88508	DNM3A_MOUSE	Mus musculus	3	0.7009
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7007

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