3beta-(beta-D-glucopyranosyloxy)-olean-12-ene-23,28,30-trioic acid - Compound Card

3beta-(beta-D-glucopyranosyloxy)-olean-12-ene-23,28,30-trioic acid

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3beta-(beta-D-glucopyranosyloxy)-olean-12-ene-23,28,30-trioic acid

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Terpenoid
    • Subclass: Pentacyclic Triterpenoid
Canonical Smiles OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H]([C@]2(C)C(=O)O)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3C[C@](C)(CC2)C(=O)O)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C36H54O12/c1-31(28(41)42)12-14-36(30(45)46)15-13-33(3)18(19(36)16-31)6-7-21-32(2)10-9-23(35(5,29(43)44)22(32)8-11-34(21,33)4)48-27-26(40)25(39)24(38)20(17-37)47-27/h6,19-27,37-40H,7-17H2,1-5H3,(H,41,42)(H,43,44)(H,45,46)/t19-,20+,21+,22+,23-,24+,25-,26+,27-,31-,32+,33+,34+,35-,36-/m0/s1
InChIKey XKEWZDPNBGRTEL-SFBVZPQOSA-N
Formula C36H54O12
HBA 9
HBD 7
MW 678.82
Rotatable Bonds 6
TPSA 211.28
LogP 3.19
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 48
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 678.36
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus amstelodami Trichocomaceae Fungi 5054

Showing of synonyms

  • Elsbaey M, Sallam A, et al. (2019). Melanogenesis Inhibitors from the Endophytic Fungus Aspergillus amstelodami. Chem Biodivers,2019,16(8),e1900237. [View] [PubMed]
Pubchem: 146682840
Nmrshiftdb2: 70106987

No compound-protein relationship available.

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6

Level: 1

Mol. Weight: 678.82 g/mol

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 678.82 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 678.82 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.08
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.730
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
55.12

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.550
Plasma Protein Binding
91.03
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
0.710
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-5.890
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.740
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.310
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
-108084.930
Rat (Acute)
2.230
Rat (Chronic Oral)
3.220
Fathead Minnow
148.260
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
8006.890
Hydration Free Energy
-2.920
Log(D) at pH=7.4
-0.870
Log(P)
2.56
Log S
-3.9
Log(Vapor Pressure)
-243.88
Melting Point
308.22
pKa Acid
4.07
pKa Basic
7.31
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8698
Ficolin-2 Q15485 FCN2_HUMAN Homo sapiens 3 0.7605
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7444
Calpain-9 O14815 CAN9_HUMAN Homo sapiens 4 0.7090

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