Cholest-5-ene-3 beta-ol-sulphate - Compound Card

Cholest-5-ene-3 beta-ol-sulphate

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Cholest-5-ene-3 beta-ol-sulphate

Structure
Zoomed Structure
  • Family: Diadematidae
  • Kingdom: Plantae
  • Class: Steroid
Canonical Smiles CC(CCC[C@H](C1CCC2[C@]1(C)CCC1C2CC=C2[C@]1(C)CC[C@@H](C2)OOS(=O)(=O)O)C)C
InChI InChI=1S/C27H46O5S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32-33(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30)/t19-,21+,22?,23?,24?,25?,26+,27-/m1/s1
InChIKey XWINWJRXFGRXJN-DXMGKPOZSA-N
Formula C27H46O5S
HBA 4
HBD 1
MW 482.73
Rotatable Bonds 8
TPSA 72.83
LogP 7.15
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 482.31
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Diadema setosum Diadematidae Plantae 31175

Showing of synonyms

  • Abdelkarem F.M, Desoky E.K, et al. (2022). Diadema setosum: isolation of bioactive secondary metabolites with cytotoxic activity toward human cervical cancer. Natural product research, 2022, 36(4), 1118-1122. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 230.39 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.4
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.96
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.96

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.45
Plasma Protein Binding
76.41
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
Non-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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
0.88
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.43
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.21
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
3.99
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
-94.05
Rat (Acute)
1.94
Rat (Chronic Oral)
2.29
Fathead Minnow
3.98
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
454.97
Hydration Free Energy
-2.03
Log(D) at pH=7.4
5.7
Log(P)
5.33
Log S
-3.59
Log(Vapor Pressure)
-8.31
Melting Point
179.46
pKa Acid
4.29
pKa Basic
7.03
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9355
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9020
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8808
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8725
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8565
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.8454
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.8336
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8320
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8285
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8247
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8212
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8166
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8165
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8149
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8066
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7914
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.7877
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7783
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7740
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7567
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7495
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7481
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7426
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7424
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7362
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7326
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7322
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7319
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7225
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7129
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7011

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