3alpha-hydroxylup-20(29)-ene-23,28-dioic acid 23-O-beta-D-glucopyranosyl ester - Compound Card

3alpha-hydroxylup-20(29)-ene-23,28-dioic acid 23-O-beta-D-glucopyranosyl ester

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3alpha-hydroxylup-20(29)-ene-23,28-dioic acid 23-O-beta-D-glucopyranosyl ester

Structure
Zoomed Structure
  • Family: Plantae - Araliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Lupane-Type Triterpene Glycosyl Ester
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)CCC[C@@]1(C)C(=O)O)C(=O)O[C@]1(O)OC(CO)[C@H](C([C@@H]1O)O)O
InChI InChI=1S/C37H58O10/c1-7-20(2)21-11-16-36(31(44)47-37(45)29(41)28(40)27(39)23(19-38)46-37)18-17-34(5)22(26(21)36)9-10-25-32(3)13-8-14-33(4,30(42)43)24(32)12-15-35(25,34)6/h21-29,38-41,45H,2,7-19H2,1,3-6H3,(H,42,43)/t21-,22+,23?,24+,25+,26+,27+,28?,29-,32-,33+,34+,35+,36-,37+/m0/s1
InChIKey BCQSGNWEENITCU-GOOQHNOJSA-N
Formula C37H58O10
HBA 9
HBD 6
MW 662.86
Rotatable Bonds 6
TPSA 173.98
LogP 4.15
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 47
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 662.4
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: 162921479
Nmrshiftdb2: 70089217

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(=O)C23C(CCC2)C4C(CC3)C5C(CC4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 662.86 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 662.86 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 662.86 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
-5.17
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
49.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.26
Plasma Protein Binding
111.14
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
3.81
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-4.51
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.66
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.79
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
-89811.32
Rat (Acute)
2.9
Rat (Chronic Oral)
3.59
Fathead Minnow
127.16
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
6159.11
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.91
Log(P)
4.29
Log S
-3.95
Log(Vapor Pressure)
-184.95
Melting Point
249.05
pKa Acid
3.73
pKa Basic
7.28
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9414
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9414
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8488
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8488
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8363
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8363
4-alpha-glucanotransferase O87172 MALQ_THETH Thermus thermophilus 3 0.7613
4-alpha-glucanotransferase O87172 MALQ_THETH Thermus thermophilus 3 0.7613
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7421
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7421
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7338
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7338
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7300
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7300
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7263
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7263
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7119
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7119
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7097
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7097

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