3-epi-betulinic acid 3-O-sulphate - Compound Card

3-epi-betulinic acid 3-O-sulphate

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3-epi-betulinic acid 3-O-sulphate

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)OS(=O)(=O)O)C(=O)O
InChI InChI=1S/C31H50O6S/c1-8-19(2)20-11-16-31(26(32)33)18-17-29(6)21(25(20)31)9-10-23-28(5)14-13-24(37-38(34,35)36)27(3,4)22(28)12-15-30(23,29)7/h20-25H,2,8-18H2,1,3-7H3,(H,32,33)(H,34,35,36)/t20-,21+,22-,23+,24+,25+,28-,29+,30+,31-/m0/s1
InChIKey GORVQTDXHSXLKY-SLDSERKVSA-N
Formula C31H50O6S
HBA 4
HBD 2
MW 550.8
Rotatable Bonds 5
TPSA 100.9
LogP 7.31
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 550.33
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: 162817484
Nmrshiftdb2: 70089219

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 550.8 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.71
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.18
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.79
Plasma Protein Binding
97.53
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
-0.5
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.94
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.86
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
2.88
Micronucleos
Toxic
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
Toxic
T. Pyriformis
-881.84
Rat (Acute)
2.15
Rat (Chronic Oral)
2.79
Fathead Minnow
3.43
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
497.74
Hydration Free Energy
-2.9
Log(D) at pH=7.4
3.74
Log(P)
3.71
Log S
-4.95
Log(Vapor Pressure)
-11.51
Melting Point
250.2
pKa Acid
3.45
pKa Basic
7.98
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8661
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8661
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8481
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8481
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8437
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8437
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8223
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8223
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8028
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8028
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7816
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7816
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7686
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7686
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7630
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7630
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7499
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7499
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7438
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7438
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7333
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7333
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7320
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7320
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7130
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7130
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7106
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7106
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 2 0.7062
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 2 0.7062

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