Sitosterol - Compound Card

Sitosterol

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Sitosterol

Structure
Zoomed Structure
  • Family: Plantae - Myrsinaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Phytosterol
Canonical Smiles CC[C@H](C(C)C)CC[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
InChI InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21+,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChIKey KZJWDPNRJALLNS-FBZNIEFRSA-N
Formula C29H50O
HBA 1
HBD 1
MW 414.72
Rotatable Bonds 6
TPSA 20.23
LogP 8.02
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 414.39
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Azolla nilotica Azzolaceae Plantae 336974
2 Lannea alata Anacardiaceae Plantae 289715
3 Aloe berhana Asphodelaceae Plantae 1593069
4 Aloe rivae Asphodelaceae Plantae 1811902
5 Aloe megalacantha Asphodelaceae Plantae 1389516
6 Aloe pulcherima Asphodelaceae Plantae 3161391
7 Aloe arborescens Asphodelaceae Plantae 45385
8 Commiphora confusa Burseraceae Plantae 43868
9 Terminalia sericeae Combretaceae Plantae 459862
10 Escinops ellenbeckii Asteraceae Plantae
11 Vernonia auriculifera Asteraceae Plantae 3032568
12 Vernonia urticifolia Asteraceae Plantae 3032568
13 Vernonia auriculifera Asteraceae Plantae 3032568
14 Vernonia urticifolia Asteraceae Plantae 3032568
15 Antidesma venosum Euphorbiaceae Plantae 992644
16 Leucas aspera Lamiaceae Plantae 483811
17 Turraea nilotica Meliaceae Plantae 992803
18 Gardenia ternifolia Rubiaceae Plantae 1237590
19 Uvaria scheffleri Annonaceae Plantae 2588162
20 Uvaria dependens Annonaceae Plantae 1144412
21 Myrsine africana Myrsinaceae Plantae 59982

Showing of synonyms

  • Magadula JJ, Mwangomo DT, et al. (2013). A novel gama-lactone and other constituents of a Tanzanian Antidesma venosum. Spatula DD,2013,3(1),7-12. [View] [PubMed]
  • Hymete A, Rohloff J, et al. (2005). Acetylenic thiophenes from the roots of Escinops ellenbeckii from Ethiopia. Natural Product Research,2005,19(8),755-761. [View] [PubMed]
  • Okoth DA, Chenia HY, et al. (2013). Antibacterial and antioxidant activities of flavonoids from Lannea alata (Engl.) Engl. (Anacardiaceae). Phytochemistry Letters,2013,6(3),476-481. [View]
  • Awas E, Omosa LK, et al. (2016). Antioxidant activities of flavonoid aglycones from Kenyan Gardenia ternifolia Schum and Thonn. IOSR Journal of Pharmacy and Biological Sciences,2016,11(3),136-141. [View] [PubMed]
  • Irungu BN, Adipo N, et al. (2015). Antiplasmodial and cytotoxic activities of the constituents of Turraea robusta and Turraea nilotica.. Journal of Ethnopharmacology,2015,174,419-425. [View] [PubMed]
  • Arai Y, Nakagawa T, et al. (1998). Chemical constituents of aquatic fern Azolla nilotica. Phytochemistry,1998,48(3),471-474. [View]
  • Ele S, G/Yesus T, et al. (2007). Chemical studies of Leucas martinicensis. M.Sc. Thesis, Addis Ababa University, Ethiopia,2007. [View] [PubMed]
  • Dagne E, Alemu M. (1991). Constituents of the leaves of four Aloe species from Ethiopia. Bulletin of the Chemical Society of Ethiopia,1991,5(2),87-91. [View] [PubMed]
  • Manguro LO, Ugi I, et al. (2003). Dammarane triterpenes of Commiphora confusa resin. Chemical and Pharmaceutical Bulletin,2003,51(5),483-486. [View] [PubMed]
  • Joseph CC, Moshi MJ, et al. (2007). Isolation of a stilbene glycoside and other constituents of Terminalia sericeae. African Journal of Traditional, Complementary and Alternative Medicines,2007,4(4),383-386. [View] [PubMed]
  • Kiplimo JJ, Everia CA, et al. (2011). Novel polyene from Vernonia urticifolia (Asteraceae). Journal of Medicinal Plants Research,2011,5(17),4202-4211. [View] [PubMed]
  • Dagne E. (1996). Review of the chemistry of Aloes of Africa. Bulletin of the Chemical Society of Ethiopia,1996,10(1),89-103. [View] [PubMed]
  • Nkunya MH, Achenbach H, et al. (1990). Schefflerin and isoschefflerin: prenylated chalcones and other constituents of Uvaria scheffleri.. Phytochemistry,1990,29(4),1261-1264. [View] [PubMed]
  • Kiplimo JJ, Koorbanally NA. (2012). The phytochemistry and biological activity of secondary metabolites from Kenyan Vernonia and Vepris species. PhD Thesis, University of Kwazulu-Natal, South Africa,2012. [View] [PubMed]
  • Nkunya MH, Waibel R, et al. (1993). Three flavonoids from the stem bark of the antimalarial Uvaria dependens.. Phytochemistry,1993,34(3),853-856. [View] [PubMed]
  • Manguro LO, Midiwo JO, et al. (1997). Triterpenoids and steroids of Myrsine africana leaves.. Planta medica,1997,63(03),290. [View] [PubMed]
  • Kiplimo JJ, Koorbanally NA, et al. (2011). Triterpenoids from Vernonia auriculifera Hiern exhibit antimicrobial activity. African Journal of Pharmacy and Pharmacology,2011,5(8),1150-1156. [View] [PubMed]
Pubchem: 222284
Kegg Ligand: C01753
Chebi: 27693
Nmrshiftdb2: 60018437
Metabolights: MTBLC27693
Drugbank: DB14038
Bindingdb: 50218197
CPRiL: 2378
Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 414.72 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.44
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.76
Plasma Protein Binding
84.03
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
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
10.99
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.99
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
2.07
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.24
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
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
-33.8
Rat (Acute)
2.21
Rat (Chronic Oral)
1.92
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
400.5
Hydration Free Energy
-3.81
Log(D) at pH=7.4
6.87
Log(P)
9.13
Log S
-6.88
Log(Vapor Pressure)
-7.25
Melting Point
145.48
pKa Acid
13.62
pKa Basic
8.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9364
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9364
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9266
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9266
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9266
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9266
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9097
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9097
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9033
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9033
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9021
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9021
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8917
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8917
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8894
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8894
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8844
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8844
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8746
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8746
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8691
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8691
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8687
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8687
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8492
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8492
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8448
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8448
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8369
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8369
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8134
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8134
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8126
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8126
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 4 0.7801
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 4 0.7801
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7699
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7699
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7691
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7691
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.7691
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.7691
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7590
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7590
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7490
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7490
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7472
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7472
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7450
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7450
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7414
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7414
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7315
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7315
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7283
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7283
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7278
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7278
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7255
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7255
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7142
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7142
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7134
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7134
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7031
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7031
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7012
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7012
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7000
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7000

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