Ehrenasterol - Compound Card

Ehrenasterol

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Ehrenasterol

Structure
Zoomed Structure
  • Family: Animalia - Desmacellidae
  • Kingdom: Animalia
  • Class: Steroid
    • Subclass: Sterol
Canonical Smiles O=C1CC[C@]2(C(C1)CC(=O)[C@]13C2CC[C@]2([C@@]3(O1)CC[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C
InChI InChI=1S/C28H42O3/c1-17(2)18(3)7-8-19(4)22-10-14-27-26(22,6)13-11-23-25(5)12-9-21(29)15-20(25)16-24(30)28(23,27)31-27/h7-8,17-20,22-23H,9-16H2,1-6H3/b8-7+/t18-,19+,20?,22+,23?,25-,26+,27-,28-/m0/s1
InChIKey RIYZDCLBHMLZIU-BQKLCDFCSA-N
Formula C28H42O3
HBA 3
HBD 0
MW 426.64
Rotatable Bonds 4
TPSA 46.67
LogP 6.15
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 426.31
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Biemna ehrenbergi Desmacellidae Animalia 1820598

Showing of synonyms

  • Youssef DTA, Badr JM, et al. (2015). Ehrenasterol and biemnic acid; new bioactive compounds from the Red Sea sponge Biemna ehrenbergi. Phytochemistry Letters,2015,12,296-301. [View]
Pubchem: 162817302
Nmrshiftdb2: 70012487

No compound-protein relationship available.

Structure

SMILES: C1CC(=O)CC(CC2=O)C1C(C2(C345)O5)CCC3CCC4

Level: 0

Mol. Weight: 426.64 g/mol

Antimicrobial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.06
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.660
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.890
Plasma Protein Binding
68.35
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
16.950
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.970
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.770
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.460
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
Toxic
T. Pyriformis
-62.490
Rat (Acute)
1.830
Rat (Chronic Oral)
1.250
Fathead Minnow
4.090
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
461.300
Hydration Free Energy
-3.080
Log(D) at pH=7.4
5.070
Log(P)
6.27
Log S
-5.92
Log(Vapor Pressure)
-6.95
Melting Point
122.37
pKa Acid
6.49
pKa Basic
3.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8994
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8994
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8031
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8031
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7995
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7995
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7838
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7838
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7668
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7668
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7466
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7466
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7430
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7430
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7353
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7353
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7332
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7332
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7032
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7032

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