20-hydroxy,24-hydroxymethyl ecdysone - Compound Card

20-hydroxy,24-hydroxymethyl ecdysone

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20-hydroxy,24-hydroxymethyl ecdysone

Structure
Zoomed Structure
  • Family: Plantae - Malvaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Ecdysteroid
Canonical Smiles OC[C@@H](C(O)(C)C)C[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)(O)C)O
InChI InChI=1S/C28H46O8/c1-24(2,34)15(14-29)10-23(33)27(5,35)22-7-9-28(36)17-11-19(30)18-12-20(31)21(32)13-25(18,3)16(17)6-8-26(22,28)4/h11,15-16,18,20-23,29,31-36H,6-10,12-14H2,1-5H3/t15-,16?,18-,20+,21-,22?,23+,25+,26+,27+,28+/m0/s1
InChIKey IDVDSLXRLYXWHQ-ATJGKMTHSA-N
Formula C28H46O8
HBA 8
HBD 7
MW 510.67
Rotatable Bonds 6
TPSA 158.68
LogP 1.07
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 510.32
Number of Lipinski Rule Violations 2
# 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: 163048289

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 510.67 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.41
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.58
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.56
Plasma Protein Binding
70.94
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
2.68
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-4.13
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.55
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.56
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
-241.6
Rat (Acute)
4.69
Rat (Chronic Oral)
2.59
Fathead Minnow
3.65
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
530.64
Hydration Free Energy
-3.1
Log(D) at pH=7.4
1.46
Log(P)
0.53
Log S
-2.14
Log(Vapor Pressure)
-11.3
Melting Point
191.42
pKa Acid
6.17
pKa Basic
6.6
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 0.8309
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8309
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8265
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8265
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8182
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8182
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7823
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7823
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7798
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7798
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7433
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7433
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7282
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7282
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7206
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7206
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7169
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7169
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7078
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7078
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7058
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7058

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