Brevipedicelone D - Compound Card

Brevipedicelone D

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Brevipedicelone D

Structure
Zoomed Structure
  • Family: Plantae - Clusiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone-Chromone
Canonical Smiles Oc1cc(O)c2c(c1)occ(c2=O)c1ccc(c(c1)Oc1c(O)cc(c2c1occ(c2=O)O)O)O
InChI InChI=1S/C24H14O11/c25-10-4-13(27)19-18(5-10)33-7-11(21(19)31)9-1-2-12(26)17(3-9)35-23-15(29)6-14(28)20-22(32)16(30)8-34-24(20)23/h1-8,25-30H
InChIKey AJFBQBQFLLNZED-UHFFFAOYSA-N
Formula C24H14O11
HBA 11
HBD 6
MW 478.37
Rotatable Bonds 3
TPSA 191.03
LogP 3.59
Number Rings 5
Number Aromatic Rings 5
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 478.05
Number of Lipinski Rule Violations 2
# 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: c1cccc(c12)occ(c2=O)-c3cc(ccc3)Oc(ccc4)c(c45)occc5=O

Level: 2

Mol. Weight: 478.37 g/mol

Structure

SMILES: O=c1ccoc(c12)c(ccc2)Oc3ccccc3

Level: 1

Mol. Weight: 478.37 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)-c3ccccc3

Level: 1

Mol. Weight: 478.37 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 478.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 478.37 g/mol

Anti-onchocercal

Absorption

Caco-2 (logPapp)
-6.28
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.35
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.93

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.33
Plasma Protein Binding
98.35
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
Non-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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.07
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.64
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.32
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.76
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
-374.29
Rat (Acute)
2.58
Rat (Chronic Oral)
3.33
Fathead Minnow
6.14
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
663.74
Hydration Free Energy
-3.45
Log(D) at pH=7.4
2.39
Log(P)
3.5
Log S
-6.57
Log(Vapor Pressure)
-11.54
Melting Point
366.06
pKa Acid
8.7
pKa Basic
4.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9610
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9527
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.9423
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9239
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9168
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.9088
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.9060
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8964
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 3 0.8948
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8946
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8925
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.8908
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8872
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8830
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8808
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8804
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8760
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8719
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8703
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8694
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8673
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8667
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8659
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.8651
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8631
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8609
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8594
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8591
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8575
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8557
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8526
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8476
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8442
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 4 0.8418
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8389
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8373
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8353
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8351
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8343
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8287
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8277
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.8274
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8267
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8245
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8205
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8203
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8177
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8162
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8161
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8157
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8109
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.8103
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8103
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8086
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8042
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.8015
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 4 0.7996
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7952
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7931
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7915
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7912
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7901
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7900
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7883
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7869
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7865
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7854
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7830
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7822
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 4 0.7812
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7759
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7758
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7741
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7736
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7722
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7710
Karilysin D0EM77 KLY_TANFA Tannerella forsythia 3 0.7684
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7657
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7650
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7642
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7642
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7632
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7619
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7613
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7609
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7569
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7557
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7557
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.7555
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7535
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7528
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7525
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7507
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7476
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.7469
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 5 0.7464
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7462
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7460
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7440
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7433
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7416
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7409
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7402
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7400
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7396
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7380
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7378
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 4 0.7378
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7374
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7350
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7345
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7330
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7300
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7281
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7278
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7277
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7269
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7260
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7254
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7251
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7249
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7246
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7240
Pol polyprotein Q90K99 Q90K99_9HIV1 Human immunodeficiency virus 1 4 0.7234
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7232
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7224
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7214
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.7203
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7168
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7157
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7145
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7141
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7135
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7133
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7129
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7126
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7124
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7121
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7121
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7116
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7114
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7112
Thymidylate kinase Q8I4S1 Q8I4S1_PLAF7 Plasmodium falciparum 5 0.7103
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7095
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7069
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7066
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7063
Tyrosine-protein kinase ITK/TSK Q08881 ITK_HUMAN Homo sapiens 3 0.7058
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7053
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7053
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7053
Purine nucleoside phosphorylase Q8DTU4 Q8DTU4_STRMU Streptococcus mutans serotype c 4 0.7036
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7035
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7035
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7031
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7028
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7028
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7025
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7025
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 4 0.7015
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7013
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7009

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