O-methylrobustaflavone - Compound Card

O-methylrobustaflavone

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O-methylrobustaflavone

Structure
Zoomed Structure
  • Family: Plantae - Clusiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles COc1ccc(cc1c1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1)O)c1cc(=O)c2c(o1)cc(cc2O)O
InChI InChI=1S/C31H20O10/c1-39-23-7-4-15(25-11-21(36)29-19(34)9-17(33)10-26(29)41-25)8-18(23)28-20(35)13-27-30(31(28)38)22(37)12-24(40-27)14-2-5-16(32)6-3-14/h2-13,32-35,38H,1H3
InChIKey ZBOKFHZIWKIWRZ-UHFFFAOYSA-N
Formula C31H20O10
HBA 10
HBD 5
MW 552.49
Rotatable Bonds 4
TPSA 170.8
LogP 5.44
Number Rings 6
Number Aromatic Rings 6
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.03
Exact Mass 552.11
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]
Pubchem: 11757331
Nmrshiftdb2: 60079092
Bindingdb: 50457775

No compound-protein relationship available.

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)-c4cc(ccc4)-c(cc5=O)oc(c56)cccc6

Level: 3

Mol. Weight: 552.49 g/mol

Structure

SMILES: O=c1ccoc(c12)ccc(c2)-c3cc(ccc3)-c(cc4=O)oc(c45)cccc5

Level: 2

Mol. Weight: 552.49 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)-c4ccccc4

Level: 2

Mol. Weight: 552.49 g/mol

Structure

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

Level: 1

Mol. Weight: 552.49 g/mol

Structure

SMILES: O=c1ccoc(c12)ccc(c2)-c3ccccc3

Level: 1

Mol. Weight: 552.49 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 552.49 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 552.49 g/mol

Anti-onchocercal

Absorption

Caco-2 (logPapp)
-5.93
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.030
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
6.84

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.470
Plasma Protein Binding
96.7
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.650
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.790
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.510
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.650
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
Toxic
T. Pyriformis
-9026.920
Rat (Acute)
2.460
Rat (Chronic Oral)
2.970
Fathead Minnow
27.030
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
571.160
Hydration Free Energy
-3.100
Log(D) at pH=7.4
4.460
Log(P)
6.11
Log S
-8.91
Log(Vapor Pressure)
-12.42
Melting Point
393.53
pKa Acid
9.1
pKa Basic
5.54
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9760
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9497
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.9391
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9194
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9070
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8977
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8925
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8923
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8773
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8767
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8732
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8668
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8539
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.8501
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8480
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8476
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8451
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8409
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.8386
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8371
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8350
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.8350
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8342
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8314
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8296
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8292
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8283
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8241
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8212
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8060
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8054
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.8024
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7980
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7897
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7886
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7882
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7870
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7828
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7806
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7767
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7739
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7697
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7693
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7681
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7666
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7656
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7641
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7624
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7605
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7600
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7590
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7571
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7556
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7539
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7529
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7512
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 4 0.7511
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7510
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7510
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7479
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7460
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7440
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7410
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7396
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7390
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7380
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7367
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7366
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7355
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7354
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 5 0.7334
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7327
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7318
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7316
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7311
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7305
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 6 0.7302
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7297
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7259
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7256
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7242
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7237
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7224
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7217
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7216
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7214
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7199
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7174
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7172
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7166
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7143
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7136
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7116
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7112
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7107
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7100
Renin P00797 RENI_HUMAN Homo sapiens 4 0.7082
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7082
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7072
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7057
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7048
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7044
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7038
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 4 0.7030
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7027
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7027
Aldose reductase-related protein 2 P45377 ALD2_MOUSE Mus musculus 3 0.7025
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7025
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 4 0.7018
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7010

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