Details of the Drug

General Information of Drug (ID: DMR3J6S)

Drug Name
Cholesterol
Synonyms
cholesterol; 57-88-5; Cholesterin; Cholest-5-en-3beta-ol; Cholesteryl alcohol; Cholestrin; Dusoran; Cordulan; Dusoline; Cholesterine; Hydrocerin; Cholestrol; Kathro; Dythol; Lanol; Super hartolan; Provitamin D; Cholesterol base H; Lidinite; Nimco cholesterol base H; Lidinit; Wool alcohols B. P.; (-)-Cholesterol; Tegolan (VAN); Cholest-5-en-3-beta-ol; 5:6-Cholesten-3beta-ol; Tegolan; 3beta-Hydroxycholest-5-ene; 5-Cholesten-3beta-ol; Cholest-5-en-3-ol (3beta)-; 3-beta-Hydroxycholest-5-ene; (3beta)-cholest-5-en-3-ol; CCRIS 2834; Dastar; HSDB 7
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 386.7
Topological Polar Surface Area (xlogp) 8.7
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 1
Chemical Identifiers
Formula
C27H46O
IUPAC Name
(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Canonical SMILES
C[C@H](CCCC(C)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
InChI
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChIKey
HVYWMOMLDIMFJA-DPAQBDIFSA-N
Cross-matching ID
PubChem CID
5997
ChEBI ID
CHEBI:16113
CAS Number
57-88-5
DrugBank ID
DB04540
TTD ID
D02DLW
VARIDT ID
DR00036

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Cholinephosphate cytidylyltransferase (PCYT1B) TTUAIKM PCY1B_HUMAN Activator [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
ATP-binding cassette sub-family A member 12 (ABCA12) DT7LDG0 ABCAC_HUMAN Substrate [3]
Niemann-Pick C1-like protein 1 (SLC65A2) DT1UMXN NPCL1_HUMAN Substrate [4]
ATP-binding cassette sub-family G member 1 (ABCG1) DTLYEPH ABCG1_HUMAN Substrate [5]
ATP-binding cassette sub-family A member 5 (ABCA5) DT195NK ABCA5_HUMAN Substrate [6]
ATP-binding cassette sub-family A member 2 (ABCA2) DTJ4NEG ABCA2_HUMAN Substrate [7]
ATP-binding cassette sub-family A member 1 (ABCA1) DT61TWI ABCA1_HUMAN Substrate [8]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [9]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2718).
2 Regulation of CTP: phosphocholine cytidylyltransferase activity by the physical properties of lipid membranes: an important role for stored curvature strain energy. Biochemistry. 2001 Sep 4;40(35):10522-31.
3 ABCA12 regulates ABCA1-dependent cholesterol efflux from macrophages and the development of atherosclerosis. Cell Metab. 2013 Aug 6;18(2):225-38.
4 Niemann-Pick C1 Like 1 protein is critical for intestinal cholesterol absorption. Science. 2004 Feb 20;303(5661):1201-4.
5 Role of HDL, ABCA1, and ABCG1 transporters in cholesterol efflux and immune responses. Arterioscler Thromb Vasc Biol. 2010 Feb;30(2):139-43.
6 Mutations in the cholesterol transporter gene ABCA5 are associated with excessive hair overgrowth. PLoS Genet. 2014 May 15;10(5):e1004333.
7 The ATP-binding cassette transporter-2 (ABCA2) regulates cholesterol homeostasis and low-density lipoprotein receptor metabolism in N2a neuroblastoma cells. Biochim Biophys Acta. 2011 Dec;1811(12):1152-64.
8 ABCA1 redistributes membrane cholesterol independent of apolipoprotein interactions. J Lipid Res. 2003 Jul;44(7):1373-80.
9 Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51.
10 Cholesterol interaction with the daunorubicin binding site of P-glycoprotein. Biochem Biophys Res Commun. 2000 Oct 5;276(3):909-16.
11 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
12 MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8.
13 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
14 Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31.
15 Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.
16 Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92.
17 Association of genetic polymorphisms in the influx transporter SLCO1B3 and the efflux transporter ABCB1 with imatinib pharmacokinetics in patients with chronic myeloid leukemia. Ther Drug Monit. 2011 Apr;33(2):244-50.
18 Doxorubicin transport by RALBP1 and ABCG2 in lung and breast cancer. Int J Oncol. 2007 Mar;30(3):717-25.
19 Wild-type breast cancer resistance protein (BCRP/ABCG2) is a methotrexate polyglutamate transporter. Cancer Res. 2003 Sep 1;63(17):5538-43.
20 The effect of low pH on breast cancer resistance protein (ABCG2)-mediated transport of methotrexate, 7-hydroxymethotrexate, methotrexate diglutamate, folic acid, mitoxantrone, topotecan, and resveratrol in in vitro drug transport models. Mol Pharmacol. 2007 Jan;71(1):240-9.
21 Role of BCRP as a biomarker for predicting resistance to 5-fluorouracil in breast cancer. Cancer Chemother Pharmacol. 2009 May;63(6):1103-10.
22 Inhibiting the function of ABCB1 and ABCG2 by the EGFR tyrosine kinase inhibitor AG1478. Biochem Pharmacol. 2009 Mar 1;77(5):781-93.
23 The phytoestrogen genistein enhances multidrug resistance in breast cancer cell lines by translational regulation of ABC transporters. Cancer Lett. 2016 Jun 28;376(1):165-72.
24 Curcumin inhibits the activity of ABCG2/BCRP1, a multidrug resistance-linked ABC drug transporter in mice. Pharm Res. 2009 Feb;26(2):480-7.
25 Imatinib mesylate (STI571) is a substrate for the breast cancer resistance protein (BCRP)/ABCG2 drug pump. Blood. 2004 Nov 1;104(9):2940-2.
26 Fenofibric acid, an active form of fenofibrate, increases apolipoprotein A-I-mediated high-density lipoprotein biogenesis by enhancing transcription of ATP-binding cassette transporter A1 gene in a liver X receptor-dependent manner. Arterioscler Thromb Vasc Biol. 2005 Jun;25(6):1193-7.
27 Pharmacological inhibition of phosphatidylcholine biosynthesis is associated with induction of phosphatidylinositol accumulation and cytolysis of neoplastic cell lines. Cancer Res. 2000 Sep 15;60(18):5204-13.
28 Sphingosine inhibits the activity of rat liver CTP:phosphocholine cytidylyltransferase. J Biol Chem. 1990 Jul 15;265(20):11746-50.