Dinklagin C - Compound Card

Dinklagin C

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Dinklagin C

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles Oc1ccc(cc1)c1cc(=O)c2c(o1)cc(c(c2O)CC(C(=C)C)O)O
InChI InChI=1S/C20H18O6/c1-10(2)14(22)7-13-15(23)8-18-19(20(13)25)16(24)9-17(26-18)11-3-5-12(21)6-4-11/h3-6,8-9,14,21-23,25H,1,7H2,2H3
InChIKey PDONMPUBRSPUSC-UHFFFAOYSA-N
Formula C20H18O6
HBA 6
HBD 4
MW 354.36
Rotatable Bonds 4
TPSA 111.13
LogP 3.06
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.15
Exact Mass 354.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dorstenia ciliata Moraceae Plantae 2604984
2 Dorstenia dinklagei Moraceae Plantae 2604986

Showing of synonyms

  • Ngadjui BT, Dongo E, et al. (2002). Dinklagins A, B and C: three prenylated flavonoids and other constituents from the twigs of Dorstenia dinklagei.. Phytochemistry,2002, 61(1), 99-104. [View] [PubMed]
  • 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]
Pubchem: 44257866

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 354.36 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 354.36 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 354.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.5
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.990
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.55

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.940
Plasma Protein Binding
80.13
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.320
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.170
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.900
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.330
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.980
Rat (Acute)
2.500
Rat (Chronic Oral)
2.990
Fathead Minnow
4.520
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
488.860
Hydration Free Energy
-12.660
Log(D) at pH=7.4
2.830
Log(P)
3.69
Log S
-4.71
Log(Vapor Pressure)
-9.26
Melting Point
235.08
pKa Acid
7.78
pKa Basic
5.65
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 0.9794
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9492
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9491
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9299
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9288
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.9220
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9202
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9141
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9016
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.9011
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9010
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8985
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8916
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8909
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8881
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8865
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8796
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8706
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8689
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 4 0.8661
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8624
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8620
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8577
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8510
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8491
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 4 0.8486
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8486
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8485
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8374
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8369
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8365
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8352
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8301
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8299
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8291
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8285
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.8255
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8244
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8229
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.8220
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8144
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8118
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8046
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8009
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7985
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7981
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7951
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7940
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7937
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7931
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7886
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7882
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7872
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7819
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7796
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7789
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7788
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7707
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7707
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7699
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7695
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7684
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7674
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7667
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7649
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7647
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7638
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7634
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7612
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7611
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7604
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7578
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7571
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7567
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7557
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7545
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 5 0.7517
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7515
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7510
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7503
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7500
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7496
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7492
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7478
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7477
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7458
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7447
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7443
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7440
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7419
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7402
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7397
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7394
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7391
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7383
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7373
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7371
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7369
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7368
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7341
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7339
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7333
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7304
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7292
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 3 0.7290
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7288
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7286
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7274
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7269
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7265
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7246
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7240
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7222
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7221
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7219
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7208
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7190
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7189
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7178
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7175
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7169
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7149
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7147
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 3 0.7146
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7145
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7137
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7133
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7132
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7113
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7110
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7104
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.7103
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7095
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7085
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7085
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7043
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7029
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7029
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7025
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7021
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7019
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7019
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7018
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7018
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7017
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7015
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7011
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7007
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7004

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