Kaempferol-3-O-(dicoumaroyl)- glucopyranoside - Compound Card

Kaempferol-3-O-(dicoumaroyl)- glucopyranoside

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Kaempferol-3-O-(dicoumaroyl)- glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Cistaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavanol Glycoside
Canonical Smiles O=C(OO[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)/C=C/c1ccc(cc1)O)/C=C/c1ccc(cc1)O
InChI InChI=1S/C38H30O16/c39-22-9-1-19(2-10-22)5-15-28(44)50-36-32(47)33(48)37(54-53-29(45)16-6-20-3-11-23(40)12-4-20)52-38(36)51-35-31(46)30-26(43)17-25(42)18-27(30)49-34(35)21-7-13-24(41)14-8-21/h1-18,32-33,36-43,47-48H/b15-5+,16-6+/t32-,33-,36+,37+,38+/m0/s1
InChIKey ATZUYQGVDRKTSH-CQQODCHJSA-N
Formula C38H30O16
HBA 16
HBD 7
MW 742.64
Rotatable Bonds 10
TPSA 252.11
LogP 3.58
Number Rings 6
Number Aromatic Rings 5
Heavy Atom Count 54
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 742.15
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Halimium halimifolium Cistaceae Plantae 632747

Showing of synonyms

  • Kerbab K, Sansone F, et al. (2019). Halimium halimifolium: From the Chemical and Functional Characterization to a Nutraceutical Ingredient Design. Planta medica, 2019, 85(11-12), 1024-1033. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OC2C(Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5)OC(CC2)OOC(=O)C=Cc6ccccc6

Level: 4

Mol. Weight: 742.64 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2C(Oc(c3=O)coc(c34)cccc4)OC(CC2)OOC(=O)C=Cc5ccccc5

Level: 3

Mol. Weight: 742.64 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OOC(O2)CCCC2Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 742.64 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 742.64 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OOC(O2)CCCC2Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 742.64 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OOC(=O)C=Cc3ccccc3

Level: 2

Mol. Weight: 742.64 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 742.64 g/mol

Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 742.64 g/mol

Structure

SMILES: O1CCCCC1OOC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 742.64 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 742.64 g/mol

Structure

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 742.64 g/mol

Structure

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

Level: 1

Mol. Weight: 742.64 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 742.64 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 742.64 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 742.64 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.67
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
11.510
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
2235.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.070
Plasma Protein Binding
78.75
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
9.730
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-53.340
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.380
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.950
Micronucleos
Toxic
NR-AhR
Safe
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
Toxic
T. Pyriformis
-4056836.050
Rat (Acute)
2.410
Rat (Chronic Oral)
4.140
Fathead Minnow
5128.490
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
448550.230
Hydration Free Energy
-2.920
Log(D) at pH=7.4
2.670
Log(P)
4.97
Log S
-6.61
Log(Vapor Pressure)
-14780.36
Melting Point
256.6
pKa Acid
-73.16
pKa Basic
2.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9779
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.9005
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.9002
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8924
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8914
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.8865
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8863
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8737
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8650
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8650
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 3 0.8593
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8548
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8544
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8540
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8499
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8446
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8438
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 4 0.8421
Seed lectin subunit I P05045 LEC1_VIGUC Vigna unguiculata subsp. cylindrica 3 0.8393
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.8370
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8279
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8268
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8201
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8098
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8029
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7884
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7859
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7833
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7815
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7809
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7808
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7788
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7786
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7785
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7780
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7692
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7655
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7623
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 4 0.7612
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7607
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7585
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7576
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7573
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7560
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7550
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7513
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7511
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7510
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7499
Type IV pilus retractation ATPase PilT P24559 PILT_PSEAE Pseudomonas aeruginosa 3 0.7422
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7422
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7393
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7385
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7382
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7379
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7360
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 4 0.7351
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7326
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7325
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.7316
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7302
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7291
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7282
Polymerase basic protein 2 Q2LG68 Q2LG68_9INFA Influenza A virus) 4 0.7260
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7260
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7251
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7244
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7241
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7231
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7208
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7208
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 3 0.7202
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7199
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7186
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7181
Chromosome partitioning protein ParA B0ZE06 B0ZE06_ECOLX Escherichia coli 3 0.7168
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7159
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7139
Uncharacterized protein Q55S71 Q55S71_CRYNB Cryptococcus neoformans var. neoformans serotype D 3 0.7133
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7132
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7129
Dipeptidyl peptidase 4 P22411 DPP4_PIG Sus scrofa 3 0.7113
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7105
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7105
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7103
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7100
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7086
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7077
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7060
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7057
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7046
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7042
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7037
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7026
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7009
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7008

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