Calotropin - Compound Card

Calotropin

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Calotropin

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Glycoside
    • Subclass: Cardenolide Glycoside
Canonical Smiles O=C[C@]12C[C@H]3O[C@@]4(O)[C@@H](O)C[C@H](O[C@H]4O[C@@H]3C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)C
InChI InChI=1S/C29H40O9/c1-15-9-23(31)29(34)25(36-15)37-21-11-17-3-4-20-19(27(17,14-30)12-22(21)38-29)5-7-26(2)18(6-8-28(20,26)33)16-10-24(32)35-13-16/h10,14-15,17-23,25,31,33-34H,3-9,11-13H2,1-2H3/t15-,17+,18-,19+,20-,21-,22-,23+,25+,26-,27-,28+,29+/m1/s1
InChIKey OWPWFVVPBYFKBG-NYVHBPEFSA-N
Formula C29H40O9
HBA 9
HBD 3
MW 532.63
Rotatable Bonds 2
TPSA 131.75
LogP 2.0
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 532.27
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Gomphocarpus sinaicus Apocynaceae Plantae 2291033
2 Gomphocarpus sinaicus Apocynaceae Plantae 2291033

Showing of synonyms

  • El-Askary H, Holzl J, et al. (1993). Cardenolide glycosides with doubly linked sugars from Gomphocarpus sinaicus. Phytochemistry,1993,34(5),1399-1402. [View]
  • Abdel-Azim NS, Hammouda FM, et al. (1996). Re-investigation of the cardenolide glycosides from Gomphocarpus sinaicus. Phytochemistry,1996,42(2),523-529. [View]
Pubchem: 16142
Kegg Ligand: C08855
Chebi: 3329
Nmrshiftdb2: 60034100
Bindingdb: 50277173
CPRiL: 77409
Structure

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

Level: 1

Mol. Weight: 532.63 g/mol

Structure

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

Level: 0

Mol. Weight: 532.63 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 532.63 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.25
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.9
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
58.52
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
3.14
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.44
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.6
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.01
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
-2940.1
Rat (Acute)
5.0
Rat (Chronic Oral)
1.8
Fathead Minnow
9.09
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
437.78
Hydration Free Energy
-2.88
Log(D) at pH=7.4
2.71
Log(P)
1.02
Log S
-3.92
Log(Vapor Pressure)
-10.33
Melting Point
254.44
pKa Acid
5.91
pKa Basic
4.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7036
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7036
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7024
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7024

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