5alpha,8alpha-epidioxycholest-6-en-3beta ol - Compound Card

5alpha,8alpha-epidioxycholest-6-en-3beta ol

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5alpha,8alpha-epidioxycholest-6-en-3beta ol

Structure
Zoomed Structure
  • Family: Plantae - Diadematidae
  • Kingdom: Plantae
  • Class: Steroid
Canonical Smiles CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@]32OO[C@]2([C@]1(C)CC[C@@H](C2)O)C=C3)C)C
InChI InChI=1S/C27H44O3/c1-18(2)7-6-8-19(3)21-9-10-22-24(21,4)13-12-23-25(5)14-11-20(28)17-26(25)15-16-27(22,23)30-29-26/h15-16,18-23,28H,6-14,17H2,1-5H3/t19-,20+,21-,22-,23-,24-,25-,26-,27+/m1/s1
InChIKey FOISYVRNZSWLHL-MEKQHADNSA-N
Formula C27H44O3
HBA 3
HBD 1
MW 416.65
Rotatable Bonds 5
TPSA 38.69
LogP 6.45
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 416.33
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]
Pubchem: 11429981
Chebi: 65851
Nmrshiftdb2: 70001054
Metabolights: MTBLC65851

No compound-protein relationship available.

Structure

SMILES: C1CCC(C1C234)CCC3C5C(OO4)(C=C2)CCCC5

Level: 0

Mol. Weight: 416.65 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.51
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.66

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.41
Plasma Protein Binding
76.33
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
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
15.47
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.47
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.11
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.58
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
-39.95
Rat (Acute)
2.1
Rat (Chronic Oral)
1.45
Fathead Minnow
3.83
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
430.18
Hydration Free Energy
-3.41
Log(D) at pH=7.4
5.61
Log(P)
7.37
Log S
-6.5
Log(Vapor Pressure)
-7.59
Melting Point
141.2
pKa Acid
10.44
pKa Basic
7.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8976
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8933
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8750
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8447
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8326
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8255
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8253
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8149
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8144
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8139
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7982
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7873
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7810
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7796
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7723
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7697
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7672
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7615
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7589
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7553
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7527
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7458
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7391
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7323
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7280
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7278
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7256
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7230
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7228
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7200
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7192
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7167
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7163
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7152
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7109
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7087
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7085
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7052
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7030
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7018

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