Stigmasterol glucoside - Compound Card

Stigmasterol glucoside

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Stigmasterol glucoside

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi, Plantae
  • Class: Steroid
    • Subclass: Sterol Glycoside
Canonical Smiles CC[C@@H](C(C)C)/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)C
InChI InChI=1S/C35H58O6/c1-7-22(20(2)3)9-8-21(4)26-12-13-27-25-11-10-23-18-24(14-16-34(23,5)28(25)15-17-35(26,27)6)40-33-32(39)31(38)30(37)29(19-36)41-33/h8-10,20-22,24-33,36-39H,7,11-19H2,1-6H3/b9-8+/t21-,22-,24+,25+,26-,27+,28+,29-,30-,31+,32-,33-,34+,35-/m1/s1
InChIKey VWDLOXMZIGUBKM-AUGXRQBFSA-N
Formula C35H58O6
HBA 6
HBD 4
MW 574.84
Rotatable Bonds 8
TPSA 99.38
LogP 5.63
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 574.42
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Cleome droserifolia Capparaceae Plantae 511510
2 Carthamus mareoticus Asteraceae Plantae 123811
3 Myrsine africana Myrsinaceae Plantae 59982
4 Cordia millenii Boraginaceae Plantae 1549839
5 Diospyros crassiflora Ebenaceae Plantae 570480
6 Acacia polyacantha Leguminosae/Fabaceae Plantae 875646
7 Allanblackia floribunda Guttiferae Plantae 469914
8 Citrus reticulata Rutaceae Plantae 85571
9 Fagara heitzii Rutaceae Plantae —
10 Manilkara obovata Sapotaceae Plantae 362719
11 Liatris spicata Asteraceae Plantae 886939
12 Aspergillus amstelodami Trichocomaceae Fungi 5054

Showing of synonyms

  • Nkengfack AE, Azebaze GA, et al. (2002). A prenylated xanthone from Allanblackia floribunda.. Phytochemistry,2002, 60(4), 381-384. [View] [PubMed]
  • Mambe FT, Na-Iya J, et al. (2019). Antibacterial and Antibiotic Modifying Potential of Crude Extracts, Fractions, and Compounds from Acacia polyacantha Willd. against MDR Gram-Negative Bacteria.. Evidence-based complementary and alternative medicine : eCAM,2019, 2019, 7507549. [View] [PubMed]
  • Akosung E, Kenmogne SB, et al. (2021). Bioactive constituents from Manilkara obovata (Sabine & G.Don) J.H.Hemsl.. Natural product research,2021, 35(22), 4347-4356. [View] [PubMed]
  • Dongmo Zeukang R, Siwe-Noundou X, et al. (2019). Cordidepsine is A Potential New Anti-HIV Depsidone from Cordia millenii, Baker. Molecules. 2019, 24(17), 3202. [View] [PubMed]
  • Ezzat M.I, Ezzat S.M, et al. (2017). In vitro evaluation of cytotoxic activity of the ethanol extract and isolated compounds from the corms of Liatris spicata (L.) willd on HepG2. Natural product research,2017, 31(11), 1325-1328. [View] [PubMed]
  • Elsbaey M, Sallam A, et al. (2019). Melanogenesis Inhibitors from the Endophytic Fungus Aspergillus amstelodami. Chem Biodivers,2019,16(8),e1900237. [View] [PubMed]
  • Akak CM, Djama CM, et al. (2010). New coumarin glycosides from the leaves of Diospyros crassiflora (Hiern).. Fitoterapia,2010, 81(7), 873-877. [View] [PubMed]
  • Fomani M, Ngeufa Happi E, et al. (2016). Oxidative burst inhibition, cytotoxicity and antibacterial acriquinoline alkaloids from Citrus reticulate (Blanco).. Bioorganic & medicinal chemistry letters,2016, 26(2), 306-309. [View] [PubMed]
  • Mbaze LM, Lado JA, et al. (2009). Oxidative burst inhibitory and cytotoxic amides and lignans from the stem bark of Fagara heitzii (Rutaceae).. Phytochemistry,2009, 70(11-12), 1442-1447. [View] [PubMed]
  • El-Askary HI (2005). Terpenoids from Cleome droserifolia (Forssk.) Del.. Molecules,2005,10,971-977. [View] [PubMed]
  • Manguro LO, Midiwo JO, et al. (1997). Triterpenoids and steroids of Myrsine africana leaves.. Planta medica,1997,63(03),290. [View] [PubMed]
  • Amer ME, Abdallah RM, et al. (1989). Two sesquiterpene fucopyranosides from Carthamus mareoticus. Phytochemistry,1989,28(4),1263-1264. [View]
Pubchem: 6602508
Chebi: 68383
Nmrshiftdb2: 60019895
Metabolights: MTBLC68383
Bindingdb: 50357395
CPRiL: 145727
Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 574.84 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 574.84 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 574.84 g/mol

Suppressive on phagocytosis response upon activation with serum

Absorption

Caco-2 (logPapp)
-5.11
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.95
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
2.06

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.44
Plasma Protein Binding
105.41
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
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.81
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.75
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.12
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.04
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
-6822.65
Rat (Acute)
2.98
Rat (Chronic Oral)
3.02
Fathead Minnow
18.57
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
360.17
Hydration Free Energy
-2.9
Log(D) at pH=7.4
5.69
Log(P)
7.17
Log S
-5.22
Log(Vapor Pressure)
-10.37
Melting Point
181.19
pKa Acid
8.49
pKa Basic
7.16
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7887
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7887
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7823
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7823
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7767
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7767
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7382
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7382
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7184
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7184
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7176
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7176
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7092
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7092

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