Stigmasterol - Compound Card

Stigmasterol

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Stigmasterol

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Phytosterol
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
InChI InChI=1S/C29H48O/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/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChIKey HCXVJBMSMIARIN-PHZDYDNGSA-N
Formula C29H48O
HBA 1
HBD 1
MW 412.7
Rotatable Bonds 5
TPSA 20.23
LogP 7.8
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 412.37
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Hyphaene thebaica Arecaceae Plantae 115479
2 Parmentiera cereifera Bignoniaceae Plantae 163100
3 Bombax malabaricum Bombacaceae Plantae 45325
4 Campanula medium Campanulaceae Plantae 56154
5 Cleome paradoxa Capparaceae Plantae 2650045
6 Ficus auriculata Moraceae Plantae 100541
7 Limonium axillare Plumbaginaceae Plantae 114150
8 Thymelaea hirsuta Thymelaeaceae Plantae 69845
9 Ferula lutea Apiaceae Plantae 52470
10 Chrysanthemum macrocarpum Asteraceae Plantae 13422
11 Carthamus mareoticus Asteraceae Plantae 123811
12 Francoeuria crispa Asteraceae Plantae 1548540
13 Hertia cheirifolia Asteraceae Plantae 430993
14 Launaea arborescens Asteraceae Plantae 43199
15 Matricaria chamomilla Asteraceae Plantae 98504
16 Pyrethrum santolinoides Asteraceae Plantae 2072400
17 Pulicaria arabica Asteraceae Plantae 119185
18 Scorzonera undulata Asteraceae Plantae 268100
19 Conyza aegyptiaca Asteraceae Plantae 741633
20 Fagara heitzii Rutaceae Plantae —

Showing of synonyms

  • Kandil FE, Ahmed KM, et al. (2000). A new flavonoid from Limonium axillare. Archiv der Pharmazie,2000,333(8),275-277. [View] [PubMed]
  • Boutaghane N, Voutquenne-Nazabadioko L, et al. (2013). A new triterpenic diester from the aerial parts of Chrysanthemum macrocarpum. Phytochemistry Letters,2013,6,519-525. [View]
  • Assiri AMA, Ramadan MF, et al. (2014). Bioactive compounds and antiradical potential of Campanula medium lipids.. Chemistry of Natural Compounds,2014,50(6),1088-1091. [View]
  • Abdel-Sattar E, El-Monem ARA, et al. (2009). Biological and Chemical Study of Cleome paradoxa B.Br.. Pharmacognosy Research,2009,1(4),175-178. [View]
  • Hafez S, Sarg TM, et al. (1987). Caryophyllene derivatives from Pulicaria arabica. Phytochemistry,1987,26(12),3356-3358. [View]
  • Bitam F, Ciavatta ML, et al. (2008). Chemical characterisation of the terpenoid constituents of the Algerian plant Launaea arborescens. Phytochemistry,2008,69,2984-2992. [View] [PubMed]
  • Rizk AM, Rimpler H (1972). Isolation of daphnoretin and beta-sitosterol-beta-D-glucoside from Thymelea hirsuta. Phytochemistry,1972,11(1),473-475. [View]
  • Ben Salem S, Jabrane A, et al. (2013). New bioactive dihydrofuranocoumarins from the roots of the Tunisian Ferula lutea (Poir.) Maire.. Bioorganic and Medicinal Chemistry Letters,2013,23(14),4248-4252. [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]
  • Abdel-Wahab NM, Hamed ANE, et al. (2014). Phenolic acid glycosides from Parmentiera cereifera Seem. (Candle tree). Phytochemistry Letters,2014,9,74-77. [View]
  • Al Fishawy A, Zayed R, et al. (2011). Phytochemical and pharmacological studies of Ficus auriculata Lour. (Moraceae) cultivated in Egypt. Planta Medica,2011,77-PL19. [View]
  • El-Hagrassi AM, Ali MM, et al. (2011). Phytochemical investigation and biological studies of Bombax malabaricum flowers. Natural Product Research,2011,25(2),141-151. [View] [PubMed]
  • Eldahshan OA, Ayoub NA, et al. (2008). Potential superoxide anion radical scavenging activity of doum palm (Hyphaene thebaica L.) leaves extract. Records of Natural Products,2008,2(3),83-93. [View]
  • Harkati B, Akkal S, et al. (2010). Secondary metabolites from Scorzonera undulata ssp. deliciosa (Guss.) Maire (Asteracae) and their antioxidant activities. Records of Natural Products,2010,4(3),171-175. [View]
  • Abdel-Mogib M, Jakupovic J, et al. (1990). Sesquiterpene lactones and kaurane glycosides from Francoeuria crispa. Phytochemistry,1990,29(8),2581-2584. [View]
  • Zaiter L, Bouheroum M, et al. (2007). Sesquiterpene lactones and other constituents from Matricaria chamomilla L.. Biochemical Systematics and Ecology,2007,35,533-538. [View]
  • Abdel-Mogib M, Jakupovic J, et al. (1989). Sesquiterpene lactones from Pyrethrum santolinoides. Phytochemistry,1989,28(1),268-271. [View]
  • Ammar S, Edziri H, et al. (2009). Spasmolytic and anti-inflammatory effects of constituents from Hertia cheirifolia. Phytomedicine,2009,16,1156-1161. [View] [PubMed]
  • Mbarga P E, Fouotsa H, et al. (2023). Two new secondary metabolites with antibacterial activities from Conyza aegyptiaca (Asteraceae). Natural product research,2023, 37(11), 1806-1815. [View] [PubMed]
  • Amer ME, Abdallah RM, et al. (1989). Two sesquiterpene fucopyranosides from Carthamus mareoticus. Phytochemistry,1989,28(4),1263-1264. [View]
Pubchem: 5280794
Kegg Ligand: C05442
Chebi: 28824
Nmrshiftdb2: 60018452
Metabolights: MTBLC28824
Bindingdb: 50376364
CPRiL: 24163
Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 412.7 g/mol

Anti-inflammatory
Antioxidant
Antiradical potential
Antitumor
Antiviral
Spasmolytic
Suppressive on phagocytosis response upon activation with serum

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.52
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.86
Plasma Protein Binding
83.31
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
7.97
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.24
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.75
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.29
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
Toxic
T. Pyriformis
-33.94
Rat (Acute)
2.37
Rat (Chronic Oral)
1.92
Fathead Minnow
4.04
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
404.8
Hydration Free Energy
-3.8
Log(D) at pH=7.4
6.64
Log(P)
8.92
Log S
-6.94
Log(Vapor Pressure)
-7.07
Melting Point
146.75
pKa Acid
13.13
pKa Basic
7.99
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 0.9351
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9351
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9315
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9315
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9077
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9077
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9067
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9067
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9041
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9041
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8986
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8986
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8977
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8977
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8828
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8828
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8814
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8814
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8786
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8786
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8670
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8670
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.8545
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.8545
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8539
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8539
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8468
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8468
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8399
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8399
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.8024
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.8024
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7962
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7962
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7930
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7930
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7742
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7742
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7740
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7740
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.7660
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.7660
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7559
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7559
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7510
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7510
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7455
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7455
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7454
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7454
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7325
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7325
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7300
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7300
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7293
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7293
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7236
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7236
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 4 0.7212
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 4 0.7212
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7211
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7211
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7026
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7026
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7001
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7001

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