Beta-sitosterol ferulate - Compound Card

Beta-sitosterol ferulate

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Beta-sitosterol ferulate

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • 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)OC(=O)/C=C/c1ccc(c(c1)OC)O)C
InChI InChI=1S/C39H58O4/c1-8-28(25(2)3)12-9-26(4)32-15-16-33-31-14-13-29-24-30(19-21-38(29,5)34(31)20-22-39(32,33)6)43-37(41)18-11-27-10-17-35(40)36(23-27)42-7/h10-11,13,17-18,23,25-26,28,30-34,40H,8-9,12,14-16,19-22,24H2,1-7H3/b18-11+/t26-,28-,30+,31+,32-,33+,34+,38+,39-/m1/s1
InChIKey ROUSJNZGMHNWOS-OJJOFZOASA-N
Formula C39H58O4
HBA 4
HBD 1
MW 590.89
Rotatable Bonds 10
TPSA 55.76
LogP 10.0
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.72
Exact Mass 590.43
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Gleditsia caspia Trichocomaceae Fungi 66090

Showing of synonyms

  • Moussa A.Y, Sobhy H.A, et al. (2021). Caspicaiene: a new kaurene diterpene with antitubercular activity from an Aspergillus endophytic isolate in Gleditsia caspia desf. Natural Product Research,2021,35(24),5653-5664. [View] [PubMed]
CPRiL: 427172
Structure

SMILES: c1ccccc1C=CC(=O)OC(C2)CCC3C2=CCC4C3CCC(C45)CCC5

Level: 1

Mol. Weight: 590.89 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 590.89 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 590.89 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.7
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
7.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.03
Plasma Protein Binding
100.27
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Inhibitor

Excretion

Clearance
6.73
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.66
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.84
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.31
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-19094.88
Rat (Acute)
1.53
Rat (Chronic Oral)
2.42
Fathead Minnow
43.86
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
366.95
Hydration Free Energy
-2.92
Log(D) at pH=7.4
7.45
Log(P)
11.3
Log S
-7.7
Log(Vapor Pressure)
-9.75
Melting Point
161.51
pKa Acid
11.07
pKa Basic
6.7
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9524
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9469
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9348
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9299
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9150
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9130
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9116
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.9115
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9087
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9023
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8995
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8976
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8855
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8817
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8816
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8803
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8748
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8733
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8714
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8695
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8583
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8498
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8497
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8468
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8355
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8328
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8316
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8293
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8285
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8266
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8244
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8236
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8158
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8138
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8119
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8112
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8068
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8022
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7970
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7937
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7865
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7851
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7844
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7795
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7775
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7745
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7734
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7705
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7699
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7694
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7662
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7650
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7634
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7565
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7561
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7552
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7542
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7532
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7506
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7473
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7470
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7463
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7458
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7442
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7430
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7429
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7420
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7405
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7404
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7372
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7370
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7363
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7362
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7360
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7352
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7349
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7344
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7340
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7332
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7326
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7322
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7319
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7313
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7313
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7302
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7302
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7296
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7292
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 4 0.7290
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7268
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7267
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7266
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7266
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7257
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7241
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7221
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7219
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7213
DNA (cytosine-5)-methyltransferase 3A O88508 DNM3A_MOUSE Mus musculus 3 0.7183
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7179
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7176
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7166
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7166
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7158
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7157
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7155
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7150
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 4 0.7149
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7148
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7138
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7136
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7127
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 3 0.7120
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7118
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7108
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7106
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7103
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7102
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7094
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7091
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7078
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7069
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7066
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7064
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7062
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 2 0.7060
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7053
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7052
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7048
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7045
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7043
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 2 0.7042
Transitional endoplasmic reticulum ATPase P55072 TERA_HUMAN Homo sapiens 3 0.7037
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7034
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7034
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7032
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7025
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7017
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7012
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7012
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7010
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7009
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7001

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