Kaempferol 3-O-alpha-L-rhamnopyranosyl-(1→2)-beta-D-glucopyranoside - Compound Card

Kaempferol 3-O-alpha-L-rhamnopyranosyl-(1→2)-beta-D-glucopyranoside

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Kaempferol 3-O-alpha-L-rhamnopyranosyl-(1→2)-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Ebenaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavanol Glucoside
Canonical Smiles OC[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)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
InChI InChI=1S/C27H30O15/c1-9-17(32)20(35)22(37)26(38-9)42-25-21(36)18(33)15(8-28)40-27(25)41-24-19(34)16-13(31)6-12(30)7-14(16)39-23(24)10-2-4-11(29)5-3-10/h2-7,9,15,17-18,20-22,25-33,35-37H,8H2,1H3/t9-,15-,17-,18-,20+,21+,22+,25-,26-,27+/m0/s1
InChIKey OHOBPOYHROOXEI-LMOIZVRRSA-N
Formula C27H30O15
HBA 15
HBD 9
MW 594.52
Rotatable Bonds 6
TPSA 249.2
LogP -1.39
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 594.16
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Diospyros crassiflora Ebenaceae Plantae 570480

Showing of synonyms

  • Akak CM, Djama CM, et al. (2010). New coumarin glycosides from the leaves of Diospyros crassiflora (Hiern).. Fitoterapia,2010, 81(7), 873-877. [View] [PubMed]
Pubchem: 162948194
Nmrshiftdb2: 60080477

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

Structure

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

Level: 2

Mol. Weight: 594.52 g/mol

Structure

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

Level: 1

Mol. Weight: 594.52 g/mol

Structure

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

Level: 1

Mol. Weight: 594.52 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 594.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 594.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.65
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.320
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
6.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.830
Plasma Protein Binding
71.43
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.210
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.870
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.920
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.380
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-9244.530
Rat (Acute)
2.350
Rat (Chronic Oral)
4.290
Fathead Minnow
20.420
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
524.710
Hydration Free Energy
-3.130
Log(D) at pH=7.4
-0.380
Log(P)
0.28
Log S
-4.37
Log(Vapor Pressure)
-13.01
Melting Point
196.61
pKa Acid
4.13
pKa Basic
6.59
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9128
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8878
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8730
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8447
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8347
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8195
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8133
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8113
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8032
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8015
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7958
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7887
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7848
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7759
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7719
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7643
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7627
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7607
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7473
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7389
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7382
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7233
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7233
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7225
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7163

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