3-O-[3-O-acetyl-6-O-(p-coumaroyl)-beta-D-glucopyranosyl]-kaempferol - Compound Card

3-O-[3-O-acetyl-6-O-(p-coumaroyl)-beta-D-glucopyranosyl]-kaempferol

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3-O-[3-O-acetyl-6-O-(p-coumaroyl)-beta-D-glucopyranosyl]-kaempferol

Structure
Zoomed Structure
  • Family: Plantae - Caprifoliaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Glycoside
Canonical Smiles CC(=O)OCC1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)[C@H](C([C@@H]1O)OC(=O)/C=C/c1ccc(cc1)O)C
InChI InChI=1S/C33H30O13/c1-16-30(45-26(39)12-5-18-3-8-20(35)9-4-18)28(40)25(15-42-17(2)34)44-33(16)46-32-29(41)27-23(38)13-22(37)14-24(27)43-31(32)19-6-10-21(36)11-7-19/h3-14,16,25,28,30,33,35-38,40H,15H2,1-2H3/b12-5+/t16-,25?,28+,30?,33-/m0/s1
InChIKey WZJMTVGTYHDIHA-BRVUYSOVSA-N
Formula C33H30O13
HBA 13
HBD 5
MW 634.59
Rotatable Bonds 8
TPSA 202.42
LogP 3.57
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 46
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 634.17
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Scabiosa stellata Caprifoliaceae Plantae 596806

Showing of synonyms

  • Lehbili M, Alabdul Magid A, et al. (2018). Triterpenoid saponins from Scabiosa stellata collected in North-eastern Algeria. Phytochemistry, 2018, 150, 40-49. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 634.59 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 634.59 g/mol

Structure

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

Level: 2

Mol. Weight: 634.59 g/mol

Structure

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

Level: 1

Mol. Weight: 634.59 g/mol

Structure

SMILES: C1COCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 634.59 g/mol

Structure

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

Level: 1

Mol. Weight: 634.59 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 634.59 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 634.59 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 634.59 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.46
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.84
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
35.35

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.08
Plasma Protein Binding
72.34
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
10.61
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.6
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.23
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.74
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
Safe
T. Pyriformis
-64367.25
Rat (Acute)
2.49
Rat (Chronic Oral)
3.36
Fathead Minnow
100.63
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
918.71
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.14
Log(P)
4.7
Log S
-6.37
Log(Vapor Pressure)
-90.53
Melting Point
232.02
pKa Acid
7.49
pKa Basic
2.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9768
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9375
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9161
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.9013
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8967
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8876
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8754
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8749
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.8741
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8644
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8578
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8555
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8484
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8466
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8418
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8346
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8229
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8045
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8021
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8017
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7968
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7934
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7917
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7849
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7843
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7828
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7795
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7785
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7769
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7740
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7696
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7630
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 3 0.7598
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7522
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7512
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7376
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7364
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7327
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7318
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7317
Copper-transporting ATPase Q97UU7 Q97UU7_SACS2 Saccharolobus solfataricus 4 0.7316
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7308
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7285
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7280
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7276
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7255
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7254
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7222
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7215
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7211
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7205
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7197
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7192
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7190
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7167
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7166
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7152
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7114
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7111
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7111
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7104
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7081
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7065
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7062
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7050
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7050
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7043
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7035
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7035
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7033
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7006
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7004
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7003

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