(22E)-ergosta-5,8,22-trien-7-one-3beta-ol - Compound Card

(22E)-ergosta-5,8,22-trien-7-one-3beta-ol

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(22E)-ergosta-5,8,22-trien-7-one-3beta-ol

Structure
Zoomed Structure
  • Family: Animalia - Desmacellidae
  • Kingdom: Animalia
  • Class: Steroid
    • Subclass: Sterol
Canonical Smiles O[C@H]1CC[C@]2(C(=CC(=O)C3=C2CC[C@]2(C3CC[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C1)C
InChI InChI=1S/C28H42O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-26-24(12-14-28(22,23)6)27(5)13-11-21(29)15-20(27)16-25(26)30/h7-8,16-19,21-23,29H,9-15H2,1-6H3/b8-7+/t18-,19+,21-,22+,23?,27-,28+/m0/s1
InChIKey UOHNARRKDSHFLD-YWHRLBDXSA-N
Formula C28H42O2
HBA 2
HBD 1
MW 410.64
Rotatable Bonds 4
TPSA 37.3
LogP 6.65
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 410.32
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: 134816354
Nmrshiftdb2: 70012488

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3=C2C(=O)C=C4C3CCCC4

Level: 0

Mol. Weight: 410.64 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.6
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)
1.92
Plasma Protein Binding
91.37
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
5.38
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.27
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.44
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.57
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
Safe
T. Pyriformis
-29.12
Rat (Acute)
3.3
Rat (Chronic Oral)
1.67
Fathead Minnow
4.53
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
453.44
Hydration Free Energy
-4.32
Log(D) at pH=7.4
5.27
Log(P)
7.09
Log S
-6.03
Log(Vapor Pressure)
-7.37
Melting Point
151.34
pKa Acid
10.62
pKa Basic
5.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9288
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9288
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9148
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9148
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8867
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8867
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8762
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8762
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8754
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8754
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8646
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8646
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8620
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8620
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8585
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8585
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.8466
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.8466
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8338
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8338
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8276
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8276
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8197
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8197
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8146
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8146
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7981
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7981
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7895
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7895
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7843
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7843
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7818
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7818
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7741
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7741
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7691
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7691
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7599
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7599
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7426
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7426
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7293
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7293
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7193
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7193
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7149
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7149
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 4 0.7120
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 4 0.7120
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7115
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7115
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7099
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7099
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7029
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7029

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