5alpha,8alpha-epidioxycholest-6,9(11)-en-3beta ol - Compound Card

5alpha,8alpha-epidioxycholest-6,9(11)-en-3beta ol

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5alpha,8alpha-epidioxycholest-6,9(11)-en-3beta ol

Structure
Zoomed Structure
  • Family: Plantae - Diadematidae
  • Kingdom: Plantae
  • Class: Steroid
Canonical Smiles CC(CCC[C@H](C1CCC2[C@]1(C)CC=C1[C@]32OO[C@]2([C@]1(C)CC[C@@H](C2)O)C=C3)C)C
InChI InChI=1S/C27H42O3/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/h12,15-16,18-22,28H,6-11,13-14,17H2,1-5H3/t19-,20+,21?,22?,24-,25-,26-,27+/m1/s1
InChIKey ROVBLBTUXSRVKA-RZFJMFOZSA-N
Formula C27H42O3
HBA 3
HBD 1
MW 414.63
Rotatable Bonds 5
TPSA 38.69
LogP 6.37
Number Rings 6
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 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]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C1C234)CC=C2C5C(OO4)(C=C3)CCCC5

Level: 0

Mol. Weight: 414.63 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.5
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.47
Plasma Protein Binding
72.63
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
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
13.42
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.26
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.25
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.98
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
-40.7
Rat (Acute)
2.44
Rat (Chronic Oral)
1.56
Fathead Minnow
3.92
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
422.7
Hydration Free Energy
-3.5
Log(D) at pH=7.4
5.19
Log(P)
7.35
Log S
-6.28
Log(Vapor Pressure)
-7.28
Melting Point
128.52
pKa Acid
9.9
pKa Basic
6.95
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 0.9069
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9063
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9035
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8969
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8833
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8828
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8810
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8392
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8137
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8059
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7995
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7932
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7697
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7679
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7671
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7650
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7637
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7629
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7617
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7603
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7584
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7520
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7515
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7493
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7462
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7453
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7428
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7397
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7285
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7282
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7207
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7184
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7112
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7094
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7079
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7046
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7029
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7019

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