Beta-sitosterol - Compound Card

Beta-sitosterol

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Beta-sitosterol

Structure
Zoomed Structure
  • Family: Plantae - Sapotaceae
  • Kingdom: Plantae, Animalia
  • Class: Steroid
    • Subclass: Phytosterol
Canonical Smiles CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)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-VJSFXXLFSA-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 Agave decipiens Agavaceae Plantae 2695036
2 Periploca laevigata Apocynaceae Plantae 413294
3 Solenostemma argel Apocynaceae Plantae 219273
4 Sabal causiarum Arecaceae Plantae 469726
5 Hyphaene thebaica Arecaceae Plantae 115479
6 Parmentiera cereifera Bignoniaceae Plantae 163100
7 Callyspongia aff. implexa Callyspongiidae Animalia 178537
8 Campanula medium Campanulaceae Plantae 56154
9 Helianthemum sessiliflorum Cistaceae Plantae 2650562
10 Euphorbia guyoniana Euphorbiaceae Plantae 1138347
11 Euphorbia helioscopia Euphorbiaceae Plantae 154990
12 Euphorbia bupleuroides Euphorbiaceae Plantae 1532838
13 Limonium axillare Plumbaginaceae Plantae 114150
14 Eragrostis tef Poaceae Plantae 110835
15 Salix subserrata Salicaceae Plantae 753747
16 Ammi majus Apiaceae Plantae 48026
17 Ferula lutea Apiaceae Plantae 52470
18 Bunium incrassatum Apiaceae Plantae 1094602
19 Aloe sinkatana Asphodelaceae Plantae 210945
20 Lantana montevidensis Verbenaceae Plantae 1241423
21 Chrysanthemum macrocarpum Asteraceae Plantae 13422
22 Centaurea africana Asteraceae Plantae 2950952
23 Centaurea omphalotricha Asteraceae Plantae 41503
24 Echinops galalensis Asteraceae Plantae 32194
25 Francoeuria crispa Asteraceae Plantae 1548540
26 Gaillardia aristata Asteraceae Plantae 55624
27 Inula crithmoides Asteraceae Plantae 119182
28 Lactuca sativa Asteraceae Plantae 4236
29 Pulicaria arabica Asteraceae Plantae 119185
30 Scorzonera undulata Asteraceae Plantae 268100
31 Sonchus macrocarpus Asteraceae Plantae 2984305
32 Hypericum quartinianum Hypericaceae Plantae 1137015
33 Raphia vinifera Arecaceae Plantae 1966430
34 Conyza aegyptiaca Asteraceae Plantae 741633
35 Symphonia globulifera Clusiaceae Plantae 156483
36 Symphonia globulifera Guttiferae Plantae 156483
37 Fagara heitzii Rutaceae Plantae
38 Baillonella toxisperma (Pierre) Sapotaceae Plantae 568230

Showing of synonyms

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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

Antimicrobial
Antioxidant
Antiradical potential
Antitumor
Antiviral
Cytotoxic
Protective against ccl4-induced injury on the human hepatoma cell line (huh7)
Suppressive on phagocytosis response upon activation with serum

Absorption

Caco-2 (logPapp)
-4.96
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
-2.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.76
Plasma Protein Binding
83.49
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
10.95
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.02
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
6.22
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
-33.89
Rat (Acute)
2.19
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
407.0
Hydration Free Energy
-3.84
Log(D) at pH=7.4
6.64
Log(P)
8.99
Log S
-6.92
Log(Vapor Pressure)
-7.25
Melting Point
142.71
pKa Acid
13.6
pKa Basic
8.5
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9594
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9500
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.9465
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9455
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.9413
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9406
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9403
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9346
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9288
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9288
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9237
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9199
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9188
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9166
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9153
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9134
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9131
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9121
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9114
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9099
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9096
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9073
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9038
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9012
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8955
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8937
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8927
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8903
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8896
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.8752
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8697
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8688
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8627
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8613
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8610
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8549
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8543
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8529
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8308
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8242
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8232
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8206
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.8193
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8191
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8186
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.8181
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.8139
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.8075
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8045
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8013
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8009
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8002
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7957
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7921
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.7881
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7838
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.7774
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7748
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7650
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7645
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7623
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7620
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7616
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7571
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7509
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7503
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.7499
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7473
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.7458
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7455
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7445
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7444
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7433
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7408
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7407
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7406
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7393
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7361
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7356
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7343
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7333
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7271
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7257
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7250
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 4 0.7245
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7244
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7235
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7230
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7226
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7209
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7189
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7159
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7114
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7107
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7103
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7099
Apocarotenoid-15,15'-oxygenase P74334 ACOX_SYNY3 Synechocystis sp 5 0.7089
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7069
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7063
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7045
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7003

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