5alpha-pregna-3beta-acetoxy-12beta,16beta-diol-20-one - Compound Card

5alpha-pregna-3beta-acetoxy-12beta,16beta-diol-20-one

Select a section from the left sidebar

5alpha-pregna-3beta-acetoxy-12beta,16beta-diol-20-one

Structure
Zoomed Structure
  • Family: Animalia - Microcionidae
  • Kingdom: Animalia
  • Class: Steroid
    • Subclass: Pregnane Steroid
Canonical Smiles CC(=O)O[C@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2C[C@@H](O)[C@]2([C@H]1C[C@@H]([C@@H]2C(=O)C)O)C)C
InChI InChI=1S/C23H36O5/c1-12(24)21-19(26)10-18-16-6-5-14-9-15(28-13(2)25)7-8-22(14,3)17(16)11-20(27)23(18,21)4/h14-21,26-27H,5-11H2,1-4H3/t14-,15-,16+,17-,18-,19-,20+,21-,22-,23+/m0/s1
InChIKey XAKNMTJKMPVPIR-PATNUSEFSA-N
Formula C23H36O5
HBA 5
HBD 2
MW 392.54
Rotatable Bonds 2
TPSA 83.83
LogP 3.11
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.91
Exact Mass 392.26
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Echinoclathria gibbosa Microcionidae Animalia 1336920

Showing of synonyms

  • Mohamed GA, Abd-Elrazek AEE, et al. (2014). New compounds from the Red Sea marine sponge Echinoclathria gibbosa. Phytochemistry Letters,2014,9,51-58. [View]
Pubchem: 102138450
Nmrshiftdb2: 70067245

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 392.54 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.52
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.55
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.22

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.72
Plasma Protein Binding
71.7
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
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
11.5
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.34
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.1
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.1
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-11.46
Rat (Acute)
2.17
Rat (Chronic Oral)
1.69
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
457.23
Hydration Free Energy
-5.09
Log(D) at pH=7.4
2.69
Log(P)
2.74
Log S
-4.08
Log(Vapor Pressure)
-8.34
Melting Point
194.19
pKa Acid
9.84
pKa Basic
5.91
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 0.9099
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9099
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8578
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8578
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8289
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8289
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7977
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7977
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7906
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7906
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7904
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7904
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7881
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7881
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7732
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7732
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7730
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7730
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7721
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7721
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7630
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7630
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7595
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7595
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7573
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7573
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7536
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7536
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7409
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7409
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7364
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7364
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7346
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7346
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7269
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7269
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7148
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7148

Download SDF