20-hydroxyecdysone-20,22-monoacetonide - Compound Card

20-hydroxyecdysone-20,22-monoacetonide

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20-hydroxyecdysone-20,22-monoacetonide

Structure
Zoomed Structure
  • Family: Plantae - Malvaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Ecdysteroid
Canonical Smiles CO[C@@H]([C@@](C1CC[C@@]2([C@]1(C)CCC1C2=CC(=O)[C@H]2[C@]1(C)C[C@H](O)[C@@H](C2)O)O)(OC)C)CCC(O)(C)C
InChI InChI=1S/C29H48O7/c1-25(2,33)11-10-24(35-6)28(5,36-7)23-9-13-29(34)18-14-20(30)19-15-21(31)22(32)16-26(19,3)17(18)8-12-27(23,29)4/h14,17,19,21-24,31-34H,8-13,15-16H2,1-7H3/t17?,19-,21+,22-,23?,24+,26+,27+,28+,29+/m0/s1
InChIKey IOUJVEYJNDNYSD-KFRHBURISA-N
Formula C29H48O7
HBA 7
HBD 4
MW 508.7
Rotatable Bonds 7
TPSA 116.45
LogP 3.16
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 508.34
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Sida spinosa Malvaceae Plantae 108380

Showing of synonyms

  • Darwish FM, Reinecke MG (2003). Ecdysteroids and other constituents from Sida spinosa L. Phytochemistry,2003,62(8),1179-1184. [View] [PubMed]
Pubchem: 162999975
Nmrshiftdb2: 70039519

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2=CC(=O)C4C3CCCC4

Level: 0

Mol. Weight: 508.7 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.890
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.95

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.530
Plasma Protein Binding
72.2
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
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
8.110
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.830
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.380
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.110
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
-277.410
Rat (Acute)
4.300
Rat (Chronic Oral)
2.050
Fathead Minnow
3.850
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
495.340
Hydration Free Energy
-2.810
Log(D) at pH=7.4
2.600
Log(P)
1.99
Log S
-3.48
Log(Vapor Pressure)
-8.65
Melting Point
186.03
pKa Acid
8.42
pKa Basic
6.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8599
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8599
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8090
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8090
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7659
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7659
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7639
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7639
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7358
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7358
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7056
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7056
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7055
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7055

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