6alpha-hydroxy-cholest-4-ene-3-one - Compound Card

6alpha-hydroxy-cholest-4-ene-3-one

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6alpha-hydroxy-cholest-4-ene-3-one

Structure
Zoomed Structure
  • Family: Plantae - Hypneaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Ketosterol
Canonical Smiles CC(CCCC([C@H]1CCC2[C@]1(C)CCC1C2C[C@@H](C2=CC(=O)CC[C@]12C)O)C)C
InChI InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-16-25(29)24-15-19(28)11-13-27(24,5)23(20)12-14-26(21,22)4/h15,17-18,20-23,25,29H,6-14,16H2,1-5H3/t18?,20?,21-,22?,23?,25+,26-,27-/m1/s1
InChIKey VUCDSTCRVYGRSG-CDYNIFSVSA-N
Formula C27H44O2
HBA 2
HBD 1
MW 400.65
Rotatable Bonds 5
TPSA 37.3
LogP 6.57
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 400.33
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Hypnea musciformis Hypneaceae Plantae 31429

Showing of synonyms

  • Bultel-Poncé V, Etahiri S, et al. (2002). New ketosteroids from the red alga Hypnea musciformis.. Bioorganic & medicinal chemistry letters, 2002, 12(13), 1715-8. [View] [PubMed]
Pubchem: 162937699

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCC(=O)C4

Level: 0

Mol. Weight: 400.65 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
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
-2.96

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.61
Plasma Protein Binding
75.5
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
13.96
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.1
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.38
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.15
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-16.87
Rat (Acute)
2.2
Rat (Chronic Oral)
1.78
Fathead Minnow
4.01
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
431.48
Hydration Free Energy
-3.85
Log(D) at pH=7.4
5.73
Log(P)
6.2
Log S
-5.97
Log(Vapor Pressure)
-7.31
Melting Point
141.83
pKa Acid
11.75
pKa Basic
7.31
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8863
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.8744
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8270
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8195
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8190
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7993
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7923
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7879
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7852
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7821
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7818
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7740
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7716
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7708
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7676
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7671
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7637
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7550
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7546
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7493
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7442
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7295
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7293
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7273
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7258
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7200
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7178
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7167
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7142
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7123

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