3beta-O-beta-D-glucopyranosiduronic acid (1→2)-beta-D-glucopyranosyloxy]-machaerinic acid gamma-lactone - Compound Card

3beta-O-beta-D-glucopyranosiduronic acid (1→2)-beta-D-glucopyranosyloxy]-machaerinic acid gamma-lactone

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3beta-O-beta-D-glucopyranosiduronic acid (1→2)-beta-D-glucopyranosyloxy]-machaerinic acid gamma-lactone

Structure
Zoomed Structure
  • Family: Plantae - Mimosaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles OC[C@H]1OC(O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2(C3CC=C3[C@@]2(C)CC[C@]24[C@H]3CC(C)(C)[C@H](C2)OC4=O)C)C)[C@@H]([C@H]([C@@H]1O)O)OC1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C42H66O13/c1-37(2)16-21-20-8-9-25-39(5)12-11-26(38(3,4)24(39)10-13-41(25,7)40(20,6)14-15-42(21)17-27(37)54-36(42)50)53-35-33(31(48)29(46)23(19-44)52-35)55-34-32(49)30(47)28(45)22(18-43)51-34/h8,21-35,43-49H,9-19H2,1-7H3/t21-,22+,23+,24-,25?,26-,27-,28+,29+,30-,31-,32+,33+,34?,35?,39-,40+,41+,42+/m0/s1
InChIKey BPVLRRMTLFISFH-VIYYGCOLSA-N
Formula C42H66O13
HBA 13
HBD 7
MW 778.98
Rotatable Bonds 6
TPSA 204.83
LogP 2.33
Number Rings 8
Number Aromatic Rings 0
Heavy Atom Count 55
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 778.45
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Albizia gummifera Mimosaceae Plantae 1561840

Showing of synonyms

  • Debella A, Haslinger E, et al. (2000). Triterpenoid saponins and sapogenin lactones from Albizia gummifera.. Phytochemistry,2000,53(8),885-892. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O=C1OC(C2)CCC(C123)C=4C(CC3)C5C(CC4)C6C(CC5)CC(CC6)OC(OCCC7)C7OC8CCCCO8

Level: 2

Mol. Weight: 778.98 g/mol

Structure

SMILES: O=C1OC(C2)CCC(C123)C=4C(CC3)C5C(CC4)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 1

Mol. Weight: 778.98 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 778.98 g/mol

Structure

SMILES: O=C1OC(C2)CCC(C123)C=4C(CC3)C5C(CC4)C6C(CC5)CCCC6

Level: 0

Mol. Weight: 778.98 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 778.98 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.17
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
16.63
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
2947.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.89
Plasma Protein Binding
97.75
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
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
0.45
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-71.59
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.91
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
8.96
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-5349567.86
Rat (Acute)
3.8
Rat (Chronic Oral)
4.02
Fathead Minnow
6759.01
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
598673.91
Hydration Free Energy
-2.92
Log(D) at pH=7.4
4.84
Log(P)
3.34
Log S
-3.53
Log(Vapor Pressure)
-19589.9
Melting Point
236.24
pKa Acid
-95.5
pKa Basic
7.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7696
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7696
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7654
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7654
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7503
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7503
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7413
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7413
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7105
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7105
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7095
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7095

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