Gancaonin P - Compound Card

Gancaonin P

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Gancaonin P

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles CC(=CCc1c(O)cc2c(c1O)c(=O)c(c(o2)c1ccc(c(c1)O)O)O)C
InChI InChI=1S/C20H18O7/c1-9(2)3-5-11-13(22)8-15-16(17(11)24)18(25)19(26)20(27-15)10-4-6-12(21)14(23)7-10/h3-4,6-8,21-24,26H,5H2,1-2H3
InChIKey OCIIFJFJVOTFTN-UHFFFAOYSA-N
Formula C20H18O7
HBA 7
HBD 5
MW 370.36
Rotatable Bonds 3
TPSA 131.36
LogP 3.5
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.15
Exact Mass 370.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pseudarthria hookeri Leguminosae/Fabaceae Plantae 992776
2 Dorstenia ciliata Moraceae Plantae 2604984
3 Dorstenia mannii Moraceae Plantae 194258

Showing of synonyms

  • Tchamgoue J, Hafizur R, et al. (2016). Flavonoids and other constituents with insulin secretion activity from Pseudarthria hookeri. Phytochemistry Letters, 2016, 17, 181-186. [View]
  • 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]
  • Ngadjui BT, Kouam SF, et al. (2000). Prenylated flavonoids from the aerial parts of Dorstenia mannii.. Phytochemistry,2000, 55(8), 915-919. [View] [PubMed]
Pubchem: 5481966
Chebi: 175755
Nmrshiftdb2: 60031441

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 370.36 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 370.36 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 370.36 g/mol

Insulin secretory

Absorption

Caco-2 (logPapp)
-6.31
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.25
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.19

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.01
Plasma Protein Binding
90.82
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-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
7.93
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.7
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.42
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.92
Micronucleos
Toxic
NR-AhR
Toxic
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
-0.07
Rat (Acute)
2.47
Rat (Chronic Oral)
3.37
Fathead Minnow
4.55
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
533.57
Hydration Free Energy
-10.84
Log(D) at pH=7.4
2.15
Log(P)
3.71
Log S
-4.73
Log(Vapor Pressure)
-8.97
Melting Point
239.45
pKa Acid
5.02
pKa Basic
6.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9550
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9476
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9083
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9059
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8868
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8842
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8784
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8781
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.8761
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8750
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8748
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8707
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 5 0.8695
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8628
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8604
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8599
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8547
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8531
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8523
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8454
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8434
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8412
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8338
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8321
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8320
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8316
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8266
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8195
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8176
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8168
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8145
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8144
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.8138
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.8129
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8104
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8095
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8085
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8058
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8021
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.8020
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8011
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 5 0.7992
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7957
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7933
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 6 0.7926
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7879
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7876
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7854
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7853
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7774
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7758
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.7742
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7740
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7740
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7737
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7715
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 4 0.7710
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7634
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7624
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7604
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 5 0.7563
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7560
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7538
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7527
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7511
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7481
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7456
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7447
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7441
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7432
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7432
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7421
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7420
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7405
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7403
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7401
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7387
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7382
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7379
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7375
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7374
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7372
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7360
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7358
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7358
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.7321
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7306
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7303
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7289
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7259
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7259
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7259
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.7249
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7248
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7247
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7227
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7213
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7206
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7190
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7179
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7172
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7170
Replicase polyprotein 1ab P0C6X7 R1AB_CVHSA Human SARS coronavirus 4 0.7165
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7151
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7139
Ribosomal RNA large subunit methyltransferase J P37634 RLMJ_ECOLI Escherichia coli 4 0.7136
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7136
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7133
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7125
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7121
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7113
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7098
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7067
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7054
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7050
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7050
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7007

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