Stigmasterol - Compound Card

Stigmasterol

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Stigmasterol

Structure
Zoomed Structure
  • Family: Arecaceae, Thymelaeaceae, Apiaceae, Moraceae, Asteraceae-Compositae, Campanulaceae, Bignoniaceae, Capparaceae, Bombacaceae, Rutaceae, Plumbaginaceae
  • 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-Compositae Plantae 13422
11 Carthamus mareoticus Asteraceae-Compositae Plantae 123811
12 Francoeuria crispa Asteraceae-Compositae Plantae 1548540
13 Hertia cheirifolia Asteraceae-Compositae Plantae 430993
14 Launaea arborescens Asteraceae-Compositae Plantae 43199
15 Matricaria chamomilla Asteraceae-Compositae Plantae 98504
16 Pyrethrum santolinoides Asteraceae-Compositae Plantae 2072400
17 Pulicaria arabica Asteraceae-Compositae Plantae 119185
18 Scorzonera undulata Asteraceae-Compositae Plantae 268100
19 Conyza aegyptiaca Asteraceae-Compositae 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]
CPRiL: 24163
Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 230.39 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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