Cholesterol - Compound Card

Cholesterol

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Cholesterol

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae, Animalia
  • Class: Steroid
    • Subclass: Phytosterol
Canonical Smiles CC(CCC[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)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
Formula C27H46O
HBA 1
HBD 1
MW 386.66
Rotatable Bonds 5
TPSA 20.23
LogP 7.39
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 386.35
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Heteroxenia ghardaqensis Alcyoniidae Animalia 859395
2 Bombax malabaricum Bombacaceae Plantae 45325
3 Dendronephthya species Nephtheidae Animalia 51109
4 Heteroxenia ghardaqensis Xeniidae Animalia 859395
5 Aloe barbadensis Asphodelaceae Plantae 34199
6 Leucas martinicensis Lamiaceae Plantae 483832

Showing of synonyms

  • Abdel-Razik AF, Nassar MI, et al. (2015). A new cytotoxic ceramide from Heteroxenia ghardaqensis and protective effect of chloroform extract against cadmium toxicity in rats. Arabian Journal of Chemistry,2015,in press. [View]
  • Ele S, G/Yesus T, et al. (2007). Chemical studies of Leucas martinicensis. M.Sc. Thesis, Addis Ababa University, Ethiopia,2007. [View] [PubMed]
  • Elkhayat ES, Ibrahim SRM, et al. (2014). Dendronephthols A–C, new sesquiterpenoids from the Red Sea soft coral Dendronephthya sp.. Tetrahedron,2014,70(24),3822-3825. [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]
  • Dagne E. (1996). Review of the chemistry of Aloes of Africa. Bulletin of the Chemical Society of Ethiopia,1996,10(1),89-103. [View] [PubMed]
Pubchem: 5997
Kegg Ligand: C00187
Chebi: 16113
Nmrshiftdb2: 60018435
Metabolights: MTBLC16113
Drugbank: DB04540
Pdb Ligand: CLR
Bindingdb: 20192
Selleck: cholesterol
CPRiL: 5
Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 386.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.35
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.64
Plasma Protein Binding
80.11
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
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
13.18
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.07
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.65
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.9
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
Safe
T. Pyriformis
-12.57
Rat (Acute)
2.14
Rat (Chronic Oral)
1.84
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
389.93
Hydration Free Energy
-3.32
Log(D) at pH=7.4
6.69
Log(P)
8.33
Log S
-6.77
Log(Vapor Pressure)
-6.75
Melting Point
139.27
pKa Acid
13.5
pKa Basic
8.46
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 0.9356
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9356
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9301
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9301
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9173
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9173
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9143
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9143
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9060
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9060
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9002
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9002
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.8975
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.8975
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8974
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8974
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8916
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8916
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8893
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8893
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8866
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8866
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8812
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8812
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8811
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8811
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.8774
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.8774
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8705
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8705
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8685
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8685
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8672
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8672
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8644
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8644
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8571
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8571
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8562
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8562
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8538
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8538
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.8537
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.8537
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.8525
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.8525
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8474
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8474
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8169
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8169
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8129
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8129
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8093
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8093
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7994
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7994
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7961
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7961
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7808
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7808
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 4 0.7802
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 4 0.7802
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7724
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7724
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7711
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7711
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7548
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7548
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7483
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7483
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7476
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7476
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7461
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7461
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7454
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7454
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7454
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7454
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7433
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7433
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7338
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7338
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7279
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7279
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7263
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7263
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7251
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7251
Apocarotenoid-15,15'-oxygenase P74334 ACOX_SYNY3 Synechocystis sp 5 0.7230
Apocarotenoid-15,15'-oxygenase P74334 ACOX_SYNY3 Synechocystis sp 5 0.7230
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7193
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7193
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7188
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7188
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7177
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7177
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7141
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7141
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7079
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7079
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7050
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7050
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7026
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7026
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7006
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7006

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