3-epi-betulinic acid 3-O-beta-D-glucopyranoside - Compound Card

3-epi-betulinic acid 3-O-beta-D-glucopyranoside

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3-epi-betulinic acid 3-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Araliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Lupane-Type Triterpene Glycoside
Canonical Smiles CCC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@H](C1(C)C)O[C@]1(O)OC(CO)[C@H](C([C@@H]1O)O)O)C(=O)O
InChI InChI=1S/C37H60O9/c1-8-20(2)21-11-16-36(31(42)43)18-17-34(6)22(27(21)36)9-10-25-33(5)14-13-26(32(3,4)24(33)12-15-35(25,34)7)46-37(44)30(41)29(40)28(39)23(19-38)45-37/h21-30,38-41,44H,2,8-19H2,1,3-7H3,(H,42,43)/t21-,22+,23?,24-,25+,26+,27+,28+,29?,30-,33-,34+,35+,36-,37+/m0/s1
InChIKey VZVTWKSITXVTSF-OWHLBNLQSA-N
Formula C37H60O9
HBA 8
HBD 6
MW 648.88
Rotatable Bonds 6
TPSA 156.91
LogP 4.62
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 46
Formal Charge 0
Fraction CSP3 0.92
Exact Mass 648.42
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Schefflera actinophylla Araliaceae Plantae 52501

Showing of synonyms

  • Wanas AS, Matsunami K, et al. (2010). Triterpene glycosides and glucosyl esters, and a triterpene from the leaves of Schefflera actinophylla. Chemical and Pharmaceutical Bulletin,2010,58(12),1596-1601. [View] [PubMed]
Pubchem: 162817482
Nmrshiftdb2: 70089204

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCC(C5)OC6CCCCO6

Level: 1

Mol. Weight: 648.88 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 648.88 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 648.88 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.67
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.23
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
29.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.21
Plasma Protein Binding
111.36
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
2.58
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-4.52
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.64
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.48
Micronucleos
Safe
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
-53168.97
Rat (Acute)
2.86
Rat (Chronic Oral)
3.56
Fathead Minnow
81.77
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
2686.92
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.81
Log(P)
4.53
Log S
-3.88
Log(Vapor Pressure)
-64.9
Melting Point
237.94
pKa Acid
3.62
pKa Basic
7.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8822
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8822
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8603
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8603
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8264
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8264
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.8140
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.8140
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8134
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8134
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8007
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8007
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8003
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8003
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7931
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7931
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7911
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7911
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7636
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7636
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7630
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7630
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7599
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7599
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7583
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7583
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7559
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7559
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7432
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7432
Beta-glucosidase A Q08638 BGLA_THEMA Thermotoga maritima 3 0.7413
Beta-glucosidase A Q08638 BGLA_THEMA Thermotoga maritima 3 0.7413
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7291
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7291
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7289
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7289
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7282
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7282
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7279
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7279
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7226
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7226
4-alpha-glucanotransferase O87172 MALQ_THETH Thermus thermophilus 3 0.7049
4-alpha-glucanotransferase O87172 MALQ_THETH Thermus thermophilus 3 0.7049
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7043
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7043
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7022
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7022
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7016
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7016

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