Chiricanine A - Compound Card

Chiricanine A

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Chiricanine A

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Derivative
Canonical Smiles CC(=CCc1c(O)cc(cc1O)/C=C/c1ccccc1)C
InChI InChI=1S/C19H20O2/c1-14(2)8-11-17-18(20)12-16(13-19(17)21)10-9-15-6-4-3-5-7-15/h3-10,12-13,20-21H,11H2,1-2H3/b10-9+
InChIKey LJFRYKIVTYCTIO-MDZDMXLPSA-N
Formula C19H20O2
HBA 2
HBD 2
MW 280.37
Rotatable Bonds 4
TPSA 40.46
LogP 4.78
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.16
Exact Mass 280.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ficus glumosa Moraceae Plantae 182114

Showing of synonyms

  • Nana F, Sandjo LP, et al. (2012). Ceramides and cytotoxic constituents from Ficus glumosa Del. (Moraceae). J. Braz. Chem. Soc., 2012, 23(3). [View] [PubMed]
Pubchem: 11087176
Nmrshiftdb2: 70032381

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=Cc2ccccc2

Level: 1

Mol. Weight: 280.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 280.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.46
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.76
Plasma Protein Binding
64.37
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
2.92
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.81
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.04
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.57
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.13
Rat (Acute)
1.87
Rat (Chronic Oral)
2.64
Fathead Minnow
4.93
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
382.62
Hydration Free Energy
-8.9
Log(D) at pH=7.4
4.49
Log(P)
5.77
Log S
-4.99
Log(Vapor Pressure)
-7.18
Melting Point
135.11
pKa Acid
9.62
pKa Basic
8.79
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9059
Cytokinin dehydrogenase 1 Q9T0N8 CKX1_MAIZE Zea mays 3 0.8929
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8801
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8762
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8305
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8297
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8272
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8268
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8239
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8159
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 3 0.8133
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8074
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8064
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8007
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7918
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7916
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7850
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7819
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7787
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7721
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7702
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 2 0.7697
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7675
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7670
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7660
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7631
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7614
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7608
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7578
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7577
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7574
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7549
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7544
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7537
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7533
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7498
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7496
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7474
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7467
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7428
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7422
Lanosterol 14-alpha demethylase CYP51 P10614 CP51_YEAST Saccharomyces cerevisiae 3 0.7401
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7391
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7390
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7378
Poly [ADP-ribose] polymerase tankyrase-1 O95271 TNKS1_HUMAN Homo sapiens 2 0.7345
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7328
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7321
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7315
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7292
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7288
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7279
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7272
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7261
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7255
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7254
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7253
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7246
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7246
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7238
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7236
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 3 0.7198
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7191
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7172
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7140
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7137
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7135
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7133
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7117
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7088
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7078
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7071
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7070
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7058
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7052
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7047
Vitamin D3 receptor A Q9PTN2 VDRA_DANRE Danio rerio 4 0.7045
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7034
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7010
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7008
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7000
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7000

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