Calotoxin - Compound Card

Calotoxin

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Calotoxin

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Cardenolide
Canonical Smiles O=CC12CC3OC4(O)C(OC3CC1CCC1C2CCC2(C1(O)CCC2C1=CC(=O)OC1)C)OC(C(C4O)O)C
InChI InChI=1S/C29H40O10/c1-14-23(32)24(33)29(35)25(37-14)38-20-10-16-3-4-19-18(27(16,13-30)11-21(20)39-29)5-7-26(2)17(6-8-28(19,26)34)15-9-22(31)36-12-15/h9,13-14,16-21,23-25,32-35H,3-8,10-12H2,1-2H3
InChIKey LYSHVSOMKBORDM-UHFFFAOYSA-N
Formula C29H40O10
HBA 10
HBD 4
MW 548.63
Rotatable Bonds 2
TPSA 151.98
LogP 0.97
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 548.26
Number of Lipinski Rule Violations 1
# 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: 30101
Nmrshiftdb2: 80008428

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CC6C(C5)OC7C(O6)OCCC7

Level: 1

Mol. Weight: 548.63 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CC5C(C4)OC6C(O5)CCCO6

Level: 0

Mol. Weight: 548.63 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 548.63 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.93
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.66
Plasma Protein Binding
11.19
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
-0.35
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.62
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.63
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.17
Micronucleos
Toxic
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
-4565.32
Rat (Acute)
4.51
Rat (Chronic Oral)
2.1
Fathead Minnow
12.78
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
398.33
Hydration Free Energy
-2.93
Log(D) at pH=7.4
1.92
Log(P)
0.57
Log S
-2.87
Log(Vapor Pressure)
-9.49
Melting Point
227.21
pKa Acid
6.3
pKa Basic
5.94
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8352
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8179
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8022
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7848
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7837
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7282
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.7224
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7152

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