3beta-hydroxy-lup-20(29)-ene-23,28 dioic acid-23-O-beta-Dglucopyranosyl ester - Compound Card

3beta-hydroxy-lup-20(29)-ene-23,28 dioic acid-23-O-beta-Dglucopyranosyl ester

Select a section from the left sidebar

3beta-hydroxy-lup-20(29)-ene-23,28 dioic acid-23-O-beta-Dglucopyranosyl ester

Structure
Zoomed Structure
  • Family: Plantae - Amaranthaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles OCC1OC(OC(=O)[C@]2(C)[C@@H](O)CC[C@]3(C2CC[C@@]2([C@@H]3CCC3[C@@]2(C)CC[C@@]2(C3[C@@H](CC2)C(=C)C)C(=O)O)C)C)C(C(C1O)O)O
InChI InChI=1S/C36H56O10/c1-18(2)19-9-14-36(30(42)43)16-15-33(4)20(25(19)36)7-8-22-32(3)12-11-24(38)35(6,23(32)10-13-34(22,33)5)31(44)46-29-28(41)27(40)26(39)21(17-37)45-29/h19-29,37-41H,1,7-17H2,2-6H3,(H,42,43)/t19-,20?,21?,22+,23?,24-,25?,26?,27?,28?,29?,32+,33+,34+,35-,36-/m0/s1
InChIKey NRKXVXNUZGSEHB-SUQGPOMYSA-N
Formula C36H56O10
HBA 9
HBD 6
MW 648.83
Rotatable Bonds 5
TPSA 173.98
LogP 3.41
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 46
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 648.39
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Anabasis articulata Amaranthaceae Plantae 996498

Showing of synonyms

  • Gamal G, Abo-El-Seoud KA, et al. (2022). Triterpenoids from the aerial parts of Anabasis articulata (Forssk) Moq: gastroprotective effect in vivo with in silico studies, cytotoxic and antimicrobial activities. Nat Prod Res. 2022, 36(16), 4076-4084.. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(=O)C2CCCC3C2CCC4C3CCC5C4CCC(C56)CCC6

Level: 1

Mol. Weight: 648.83 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 648.83 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 648.83 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.2
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
31.35

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.05
Plasma Protein Binding
88.06
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
3.15
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.73
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.49
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.39
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-58162.75
Rat (Acute)
3.09
Rat (Chronic Oral)
3.69
Fathead Minnow
87.93
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
2933.89
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.64
Log(P)
3.57
Log S
-3.59
Log(Vapor Pressure)
-83.1
Melting Point
242.01
pKa Acid
4.29
pKa Basic
6.69
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.9151
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9109
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8671
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7346
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7211
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7178
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7177
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7079
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7077
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7076
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7045

Download SDF