12beta-hydroxycoroglaucigenin - Compound Card

12beta-hydroxycoroglaucigenin

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12beta-hydroxycoroglaucigenin

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Cardenolide
Canonical Smiles OC[C@]12CC[C@@H](C[C@@H]1CC[C@@H]1[C@@H]2C[C@@H](O)[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)O
InChI InChI=1S/C23H34O6/c1-21-16(13-8-20(27)29-11-13)5-7-23(21,28)17-3-2-14-9-15(25)4-6-22(14,12-24)18(17)10-19(21)26/h8,14-19,24-26,28H,2-7,9-12H2,1H3/t14-,15-,16+,17+,18-,19+,21-,22+,23-/m0/s1
InChIKey HTBPPXIZDUWCFX-HGSYIYTCSA-N
Formula C23H34O6
HBA 6
HBD 4
MW 406.52
Rotatable Bonds 2
TPSA 107.22
LogP 1.55
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 406.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Calotropis procera Apocynaceae Plantae 141467

Showing of synonyms

  • Mohamed N.H, Liu M, et al. (2015). Cytotoxic cardenolides from the latex of Calotropis procera. Bioorg Med Chem Lett, 2015, 25(20), 4615-20.. [View] [PubMed]
Pubchem: 11876182
Nmrshiftdb2: 70060116

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CCCC5

Level: 1

Mol. Weight: 406.52 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 406.52 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 406.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.96
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.06
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.61
Plasma Protein Binding
59.8
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
Non-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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.67
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.57
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-2.12
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.1
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-33.48
Rat (Acute)
3.46
Rat (Chronic Oral)
2.23
Fathead Minnow
3.76
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
497.7
Hydration Free Energy
-4.54
Log(D) at pH=7.4
1.35
Log(P)
0.44
Log S
-2.88
Log(Vapor Pressure)
-10.42
Melting Point
231.63
pKa Acid
7.45
pKa Basic
6.96
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 0.9101
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7398
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7230

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