7,7''-beta-diglucoside of (2S,3R)-chamaejasmin - Compound Card

7,7''-beta-diglucoside of (2S,3R)-chamaejasmin

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7,7''-beta-diglucoside of (2S,3R)-chamaejasmin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Biflavanone
Canonical Smiles OC[C@H]1OC(Oc2cc(O)c3c(c2)O[C@@H]([C@H](C3=O)[C@@H]2[C@H](Oc3c(C2=O)c(O)cc(c3)OC2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)c2ccc(cc2)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C42H42O20/c43-13-25-31(49)35(53)37(55)41(61-25)57-19-9-21(47)27-23(11-19)59-39(15-1-5-17(45)6-2-15)29(33(27)51)30-34(52)28-22(48)10-20(58-42-38(56)36(54)32(50)26(14-44)62-42)12-24(28)60-40(30)16-3-7-18(46)8-4-16/h1-12,25-26,29-32,35-50,53-56H,13-14H2/t25-,26-,29+,30+,31-,32-,35+,36+,37-,38-,39-,40-,41?,42?/m1/s1
InChIKey RVPPNKOUWPOQRX-JLDKYGFASA-N
Formula C42H42O20
HBA 20
HBD 12
MW 866.78
Rotatable Bonds 9
TPSA 332.28
LogP -0.57
Number Rings 8
Number Aromatic Rings 4
Heavy Atom Count 62
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 866.23
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Ormocarpum kirkii Leguminosae/Fabaceae Plantae 77284

Showing of synonyms

  • Nyandat E, Hassanali A, et al. (1990). The 7,7''-β-diglucoside of (2S,3R)-chamaejasmin from Ormocarpum kirkii.. Phytochemistry,1990,29(7),2361-2364. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1Oc(cc2)cc(c23)OC(c4ccccc4)C(C3=O)C(C5=O)C(c6ccccc6)Oc(c57)cc(cc7)OC8CCCCO8

Level: 5

Mol. Weight: 866.78 g/mol

Structure

SMILES: O1CCCCC1Oc(cc2)cc(c23)OC(c4ccccc4)C(C3=O)C(C5=O)COc(c56)cc(cc6)OC7CCCCO7

Level: 4

Mol. Weight: 866.78 g/mol

Structure

SMILES: O1CCCCC1Oc(cc2)cc(c23)OC(c4ccccc4)C(C3=O)C(C5=O)C(c6ccccc6)Oc(c57)cccc7

Level: 4

Mol. Weight: 866.78 g/mol

Structure

SMILES: O1CCCCC1Oc(cc2)cc(c23)OCC(C3=O)C(C4=O)COc(c45)cc(cc5)OC6CCCCO6

Level: 3

Mol. Weight: 866.78 g/mol

Structure

SMILES: O1CCCCC1Oc(cc2)cc(c23)OCC(C3=O)C(C4=O)C(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 866.78 g/mol

Structure

SMILES: O1CCCCC1Oc(cc2)cc(c23)OC(c4ccccc4)C(C3=O)C(C5=O)COc(c56)cccc6

Level: 3

Mol. Weight: 866.78 g/mol

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)C(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 866.78 g/mol

Structure

SMILES: O1CCCCC1Oc(cc2)cc(c23)OCC(C3=O)C(C4=O)COc(c45)cccc5

Level: 2

Mol. Weight: 866.78 g/mol

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)COc(c45)cccc5

Level: 2

Mol. Weight: 866.78 g/mol

Structure

SMILES: c1ccccc1C(CC2=O)Oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 866.78 g/mol

Structure

SMILES: c1cccc(c12)OCC(C2=O)C(C3=O)COc(c34)cccc4

Level: 1

Mol. Weight: 866.78 g/mol

Structure

SMILES: O=C1CCOc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 866.78 g/mol

Structure

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 866.78 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 866.78 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 866.78 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 866.78 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.47
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
999.36
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
131448.16

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.65
Plasma Protein Binding
68.34
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
Inhibitor

Excretion

Clearance
5.29
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-3053.3
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.97
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.36
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
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
-238569673.1
Rat (Acute)
2.73
Rat (Chronic Oral)
5.55
Fathead Minnow
301152.69
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
26825473.78
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-3.17
Log(P)
-0.07
Log S
-5.9
Log(Vapor Pressure)
-883230.47
Melting Point
296.66
pKa Acid
-6373.96
pKa Basic
-25.25
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9065
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9065
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8703
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8703
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8422
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8422
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 3 0.8371
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 3 0.8371
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8343
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8343
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.8317
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.8317
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8163
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8163
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7610
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7610
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7449
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7449
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7445
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7445
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7420
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7420
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7328
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7328
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7301
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7301
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7094
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7094

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