Melithasterol B - Compound Card

Melithasterol B

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Melithasterol B

Structure
Zoomed Structure
  • Family: Animalia - Desmacellidae
  • Kingdom: Animalia
  • Class: Steroid
    • Subclass: Sterol
Canonical Smiles O[C@H]1CC[C@]2([C@@]3(C1)O[C@H]3[C@H](C1=C2CC[C@]2(C1CC[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)O)C
InChI InChI=1S/C28H44O3/c1-16(2)17(3)7-8-18(4)20-9-10-21-23-22(12-13-26(20,21)5)27(6)14-11-19(29)15-28(27)25(31-28)24(23)30/h7-8,16-21,24-25,29-30H,9-15H2,1-6H3/b8-7+/t17-,18+,19-,20+,21?,24-,25-,26+,27+,28-/m0/s1
InChIKey PCIZFQVDNDHRPP-FTARVDCESA-N
Formula C28H44O3
HBA 3
HBD 2
MW 428.66
Rotatable Bonds 4
TPSA 52.99
LogP 5.66
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 428.33
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: 162999896
Nmrshiftdb2: 70012485

No compound-protein relationship available.

Structure

SMILES: C1CCCC2C(=C3CC(C124)O4)CCC5C3CCC5

Level: 0

Mol. Weight: 428.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.09
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.63
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.8

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.78
Plasma Protein Binding
57.87
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
14.61
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.45
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.72
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.16
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
-66.76
Rat (Acute)
3.16
Rat (Chronic Oral)
1.64
Fathead Minnow
4.09
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
454.65
Hydration Free Energy
-3.4
Log(D) at pH=7.4
4.58
Log(P)
6.61
Log S
-6.25
Log(Vapor Pressure)
-7.83
Melting Point
148.74
pKa Acid
8.04
pKa Basic
6.3
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 0.9256
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9256
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8958
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8958
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8672
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8672
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8446
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8446
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8421
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8421
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8419
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8419
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8329
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8329
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8062
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8062
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8035
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8035
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8002
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8002
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7953
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7953
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7856
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7856
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7591
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7591
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7586
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7586
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.7582
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.7582
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7507
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7507
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7389
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7389
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7270
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7270
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7237
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7237
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7144
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7144
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7062
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7062

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