Beta-sitosterol glucoside - Compound Card

Beta-sitosterol glucoside

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Beta-sitosterol glucoside

Structure
Zoomed Structure
  • Family: Plantae - Bignoniaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Phytosterol Glycoside
Canonical Smiles CC[C@@H](C(C)C)CC[C@H]([C@H]1CCC2[C@]1(C)CCC(C2C)[C@]1(C)CC[C@H](CC1)O[C@@H]1OC(CO)[C@@H](C([C@@H]1O)O)O)C
InChI InChI=1S/C34H62O6/c1-8-23(20(2)3)10-9-21(4)25-11-12-27-22(5)26(15-18-34(25,27)7)33(6)16-13-24(14-17-33)39-32-31(38)30(37)29(36)28(19-35)40-32/h20-32,35-38H,8-19H2,1-7H3/t21-,22?,23-,24-,25-,26?,27?,28?,29+,30?,31+,32-,33-,34-/m1/s1
InChIKey INRMYAOPWFZTEA-GSPSJMNVSA-N
Formula C34H62O6
HBA 6
HBD 4
MW 566.86
Rotatable Bonds 10
TPSA 99.38
LogP 5.93
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 1.0
Exact Mass 566.45
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Ruellia patula Acanthaceae Plantae 441006
2 Crinum augustum Amaryllidaceae Plantae 16055
3 Jacaranda mimosaefolia Bignoniaceae Plantae 185774
4 Parmentiera cereifera Bignoniaceae Plantae 163100

Showing of synonyms

  • Abdel-Wahab NM, Hamed ANE, et al. (2014). Phenolic acid glycosides from Parmentiera cereifera Seem. (Candle tree). Phytochemistry Letters,2014,9,74-77. [View]
  • Zaghloul AM, Gohar AA, et al. (2011). Phenylpropanoids from the stem bark of Jacaranda mimosaefolia. Natural Product Research,2011,25(1),68-76. [View] [PubMed]
  • Samy MN, Khalil HE, et al. (2011). Three new flavonoid glycosides, byzantionoside B 6’-O-Sulfate and xyloglucoside of (Z)-hex-3-en-1-ol from Ruellia patula. Chemical and Pharmaceutical Bulletin,2011,59(6),725-729. [View] [PubMed]
  • El-Hafiz MAA. (1990). Two keto alcohols from Crinum augustum. Phytochemistry,1990,29(12),3936-3938. [View]
Pubchem: 162822971
CPRiL: 7215
Structure

SMILES: C1CCC(C12)CCC(C2)C3CCC(CC3)OC4CCCCO4

Level: 2

Mol. Weight: 566.86 g/mol

Structure

SMILES: C1CCC(C12)CCC(C2)C3CCCCC3

Level: 1

Mol. Weight: 566.86 g/mol

Structure

SMILES: C1CCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 566.86 g/mol

Structure

SMILES: C1CCC(C12)CCCC2

Level: 0

Mol. Weight: 566.86 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 566.86 g/mol

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 566.86 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.13
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.95
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.21
Plasma Protein Binding
102.56
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
Substrate
CYP 2C9 Inhibitor
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.88
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.08
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.01
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.41
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
-3041.65
Rat (Acute)
2.49
Rat (Chronic Oral)
3.24
Fathead Minnow
9.08
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
398.65
Hydration Free Energy
-2.85
Log(D) at pH=7.4
5.71
Log(P)
7.22
Log S
-4.85
Log(Vapor Pressure)
-9.97
Melting Point
149.02
pKa Acid
8.71
pKa Basic
8.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8857
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8857
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8428
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8428
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8338
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8338
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7785
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7785
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7670
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7670
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7669
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7669
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7582
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7582
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7538
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7538
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7035
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7035

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