20-hydroxy-5alpha-cholest-22-ene-3,6-dione - Compound Card

20-hydroxy-5alpha-cholest-22-ene-3,6-dione

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20-hydroxy-5alpha-cholest-22-ene-3,6-dione

Structure
Zoomed Structure
  • Family: Plantae - Hypneaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Ketosterol
Canonical Smiles CC(CC=C[C@@]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC(=O)[C@@H]2[C@]1(C)CCC(=O)C2)(O)C)C
InChI InChI=1S/C27H42O3/c1-17(2)7-6-12-27(5,30)24-9-8-20-19-16-23(29)22-15-18(28)10-13-25(22,3)21(19)11-14-26(20,24)4/h6,12,17,19-22,24,30H,7-11,13-16H2,1-5H3/t19-,20-,21-,22+,24-,25+,26-,27-/m0/s1
InChIKey NFWKUHWWUWPAOU-NZDMORLZSA-N
Formula C27H42O3
HBA 3
HBD 1
MW 414.63
Rotatable Bonds 4
TPSA 54.37
LogP 5.75
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 414.31
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: 129774404

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CC(=O)C4C3CCC(=O)C4

Level: 0

Mol. Weight: 414.63 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.47
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.73
Plasma Protein Binding
85.06
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
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
14.15
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.46
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.78
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.26
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
Toxic
T. Pyriformis
-26.2
Rat (Acute)
2.13
Rat (Chronic Oral)
1.72
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
456.79
Hydration Free Energy
-3.76
Log(D) at pH=7.4
4.85
Log(P)
5.22
Log S
-5.47
Log(Vapor Pressure)
-8.12
Melting Point
169.37
pKa Acid
8.68
pKa Basic
4.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9033
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9004
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8780
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8574
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8496
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8156
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8062
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8058
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8042
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8012
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7965
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7917
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7691
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 4 0.7642
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7479
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7470
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7365
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7234
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7187
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7170
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7153
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7087
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7077
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7066
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7060
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7043
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7038

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