3alpha-hydroxylup-20(29)-en-23,28-dioic acid 3-O-beta-D-glucopyranoside - Compound Card

3alpha-hydroxylup-20(29)-en-23,28-dioic acid 3-O-beta-D-glucopyranoside

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3alpha-hydroxylup-20(29)-en-23,28-dioic 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]([C@@]1(C)C(=O)O)O[C@]1(O)OC(CO)[C@H](C([C@@H]1O)O)O)C(=O)O
InChI InChI=1S/C37H58O11/c1-7-19(2)20-10-15-36(31(44)45)17-16-33(4)21(26(20)36)8-9-23-32(3)13-12-25(35(6,30(42)43)24(32)11-14-34(23,33)5)48-37(46)29(41)28(40)27(39)22(18-38)47-37/h20-29,38-41,46H,2,7-18H2,1,3-6H3,(H,42,43)(H,44,45)/t20-,21+,22?,23+,24+,25+,26+,27+,28?,29-,32+,33+,34+,35-,36-,37+/m0/s1
InChIKey OBZZDHZAFZXALP-ZSKQSDCOSA-N
Formula C37H58O11
HBA 9
HBD 7
MW 678.86
Rotatable Bonds 7
TPSA 194.21
LogP 3.69
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 48
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 678.4
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: 163025978
Nmrshiftdb2: 70089226

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCC(C5)OC6CCCCO6

Level: 1

Mol. Weight: 678.86 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 678.86 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 678.86 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.92
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.73
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
69.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.96
Plasma Protein Binding
108.08
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
3.49
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-5.71
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.31
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.4
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-134481.97
Rat (Acute)
2.36
Rat (Chronic Oral)
2.81
Fathead Minnow
182.38
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
11360.33
Hydration Free Energy
-2.92
Log(D) at pH=7.4
1.08
Log(P)
3.36
Log S
-3.15
Log(Vapor Pressure)
-338.75
Melting Point
243.33
pKa Acid
2.88
pKa Basic
7.24
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 0.9017
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9017
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8864
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8864
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8438
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8438
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8356
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8356
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8324
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8324
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.8214
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.8214
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8183
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8183
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8113
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8113
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8091
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8091
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7868
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7868
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7821
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7821
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7723
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7723
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7680
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7680
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7594
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7594
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7531
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7531
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7426
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7426
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7417
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7417
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7389
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7389
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7350
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7350
Beta-glucosidase A Q08638 BGLA_THEMA Thermotoga maritima 3 0.7342
Beta-glucosidase A Q08638 BGLA_THEMA Thermotoga maritima 3 0.7342
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7340
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7340
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7308
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7308
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7276
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7276
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7274
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7274
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7235
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7235
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7037
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7037
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7011
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7011

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