Brevipediclone C - Compound Card

Brevipediclone C

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Brevipediclone C

Structure
Zoomed Structure
  • Family: Plantae - Clusiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone-Chromone
Canonical Smiles Oc1ccc(cc1)C1Oc2cc(O)c(c(c2C(=O)C1O)O)Oc1ccc(cc1)C1Oc2cc(O)c(c(c2C(=O)C1O)O)O
InChI InChI=1S/C30H22O13/c31-13-5-1-11(2-6-13)28-27(40)24(37)20-18(43-28)10-16(33)30(25(20)38)41-14-7-3-12(4-8-14)29-26(39)23(36)19-17(42-29)9-15(32)21(34)22(19)35/h1-10,26-29,31-35,38-40H
InChIKey JAUGGDIYZJADMX-UHFFFAOYSA-N
Formula C30H22O13
HBA 13
HBD 8
MW 590.49
Rotatable Bonds 4
TPSA 223.67
LogP 3.07
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 590.11
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Garcinia brevipedicellata Clusiaceae Plantae 469917

Showing of synonyms

  • Akongwi M, Tih AE, et al. (2019). Brevipedicelones D and E, Two C-O-C Flavonoid Dimmers from the Leaves of Garcinia brevipedicellata and Anti-onchocercal Activity.. Natural products and bioprospecting,2019, 9(1), 61-68. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(CC2=O)Oc(c23)ccc(c3)Oc(cc4)ccc4C(CC5=O)Oc(c56)cccc6

Level: 3

Mol. Weight: 590.49 g/mol

Structure

SMILES: O=C1CCOc(c12)ccc(c2)Oc(cc3)ccc3C(CC4=O)Oc(c45)cccc5

Level: 2

Mol. Weight: 590.49 g/mol

Structure

SMILES: c1ccccc1C(CC2=O)Oc(c23)ccc(c3)Oc4ccccc4

Level: 2

Mol. Weight: 590.49 g/mol

Structure

SMILES: O=C1CCOc(c12)ccc(c2)Oc3ccccc3

Level: 1

Mol. Weight: 590.49 g/mol

Structure

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 590.49 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 590.49 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 590.49 g/mol

Anti-onchocercal

Absorption

Caco-2 (logPapp)
-6.53
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.080
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
12.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.060
Plasma Protein Binding
68.62
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.820
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.140
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.280
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.420
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
-21457.780
Rat (Acute)
2.580
Rat (Chronic Oral)
4.160
Fathead Minnow
47.560
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
436.580
Hydration Free Energy
-3.150
Log(D) at pH=7.4
2.090
Log(P)
2.34
Log S
-5.55
Log(Vapor Pressure)
-17.16
Melting Point
302.61
pKa Acid
4.72
pKa Basic
4.43
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9495
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9178
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8891
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8819
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8664
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8616
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8602
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8510
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8487
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8468
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8461
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8446
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8430
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8424
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8385
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8373
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.8359
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 3 0.8328
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8324
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8247
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8175
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8167
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8139
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 3 0.8079
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8051
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8008
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7998
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 4 0.7994
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7962
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7961
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7930
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7927
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7925
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7917
Probable tRNA(His) guanylyltransferase Q9NWX6 THG1_HUMAN Homo sapiens 3 0.7910
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 4 0.7909
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7909
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7902
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.7867
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7816
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7812
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7801
Bifunctional AAC/APH P0A0C1 AACA_STAAU Staphylococcus aureus 4 0.7790
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7745
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7744
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7727
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7726
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7708
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7682
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7667
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7649
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7639
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7616
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7575
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7566
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7552
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7546
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7536
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7533
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7533
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7528
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7526
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7516
Glucose-1-phosphate thymidylyltransferase 1 P37744 RMLA1_ECOLI Escherichia coli 5 0.7506
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7491
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7447
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7445
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7433
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7424
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 3 0.7415
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 3 0.7404
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 3 0.7402
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7400
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 5 0.7396
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7392
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7382
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7382
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7363
Casein kinase II subunit alpha P15790 CSK21_YEAST Saccharomyces cerevisiae 4 0.7356
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 4 0.7346
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7344
Uncharacterized protein mg662 G5CQN7 G5CQN7_9VIRU Megavirus chiliensis 4 0.7340
Matrix metalloproteinase-20 O60882 MMP20_HUMAN Homo sapiens 3 0.7333
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7318
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7313
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.7309
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7300
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 5 0.7282
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7276
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7275
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7257
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 5 0.7248
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7248
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7231
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7217
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7215
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7200
Unconventional myosin-Va Q02440 MYO5A_CHICK Gallus gallus 3 0.7200
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7196
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7185
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7178
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7169
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7166
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7153
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7151
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7150
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7135
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7129
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7121
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7118
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7114
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7114
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 4 0.7102
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7101
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7099
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7092
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7089
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7067
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7066
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 2 0.7051
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7045
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7043
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7035
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7028
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7016
Alpha-2,3/2,6-sialyltransferase/sialidase Q15KI8 Q15KI8_PASMD Pasteurella multocida 4 0.7012
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7012
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.7009
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7008
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7006
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7006
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7002

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