4'-O-demethylknipholone-4'-beta-D-glucopyranoside - Compound Card

4'-O-demethylknipholone-4'-beta-D-glucopyranoside

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4'-O-demethylknipholone-4'-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles OC[C@@H]1OC(Oc2cc(O)c(c(c2C(=O)C)O)c2c(C)cc(c3c2C(=O)c2ccc(cc2C3=O)O)O)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C29H26O13/c1-9-5-14(33)21-22(23(35)12-4-3-11(32)6-13(12)24(21)36)18(9)20-15(34)7-16(19(10(2)31)26(20)38)41-29-28(40)27(39)25(37)17(8-30)42-29/h3-7,17,25,27-30,32-34,37-40H,8H2,1-2H3/t17-,25-,27+,28-,29?/m0/s1
InChIKey UUUJLOXBZJQFAK-MBKMWOIASA-N
Formula C29H26O13
HBA 13
HBD 8
MW 582.51
Rotatable Bonds 5
TPSA 231.51
LogP 0.64
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.28
Exact Mass 582.14
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Bulbine frutescens Asphodelaceae Plantae 210954

Showing of synonyms

  • Bringmann G, Mutanyatta-Comar J, et al. (2008). Joziknipholones A and B: the first dimeric phenylanthraquinones, from the roots of Bulbine frutescens. Chemistry: A European Journal,2008,14(5),1420-429. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3-c4ccc(cc4)OC5CCCCO5

Level: 2

Mol. Weight: 582.51 g/mol

Structure

SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3-c4ccccc4

Level: 1

Mol. Weight: 582.51 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 582.51 g/mol

Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 582.51 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 582.51 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 582.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.51
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.29
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
5.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.74
Plasma Protein Binding
68.77
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
10.19
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.43
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.85
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.88
Micronucleos
Toxic
NR-AhR
Toxic
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
-7529.01
Rat (Acute)
2.58
Rat (Chronic Oral)
4.38
Fathead Minnow
17.57
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
536.35
Hydration Free Energy
-3.01
Log(D) at pH=7.4
0.74
Log(P)
2.03
Log S
-6.13
Log(Vapor Pressure)
-10.15
Melting Point
247.31
pKa Acid
5.14
pKa Basic
5.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.9124
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.9124
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8466
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8466
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.8075
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.8075
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8003
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8003
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7835
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7835
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7825
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7825
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7691
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7691
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7685
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7685
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7672
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7672
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7669
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7669
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7641
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7641
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7569
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7569
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7527
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7527
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 3 0.7424
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 3 0.7424
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7387
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7387
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7335
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7335
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7264
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7264
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7169
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7169
Mitogen-activated protein kinase 14 P47811 MK14_MOUSE Mus musculus 4 0.7158
Mitogen-activated protein kinase 14 P47811 MK14_MOUSE Mus musculus 4 0.7158
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7143
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7143
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7135
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7135
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7118
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7118
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7012
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7012

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