5,6-dehydrocalotropagenin - Compound Card

5,6-dehydrocalotropagenin

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5,6-dehydrocalotropagenin

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Glycoside
    • Subclass: Cardenolide Glycoside
Canonical Smiles O=C[C@]12C[C@@H](O)C(CC1=CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)O
InChI InChI=1S/C23H30O6/c1-21-6-4-16-17(3-2-14-9-18(25)19(26)10-22(14,16)12-24)23(21,28)7-5-15(21)13-8-20(27)29-11-13/h2,8,12,15-19,25-26,28H,3-7,9-11H2,1H3/t15-,16+,17-,18?,19-,21-,22-,23+/m1/s1
InChIKey FJXWBXGFWCHFFE-LHUTUEIVSA-N
Formula C23H30O6
HBA 6
HBD 3
MW 402.49
Rotatable Bonds 2
TPSA 104.06
LogP 1.67
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.74
Exact Mass 402.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Gomphocarpus sinaicus Apocynaceae Plantae 2291033

Showing of synonyms

  • El-Askary H, Holzl J, et al. (1995). Cardenolide glycosides from Gomphocarpus sinaicus. Phytochemistry,1995,38(4),943-946. [View]
Pubchem: 162986798
Nmrshiftdb2: 70078874

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 402.49 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 402.49 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 402.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.97
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
-2.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.53
Plasma Protein Binding
47.79
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
5.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.26
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.07
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.43
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Toxic
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-30.84
Rat (Acute)
4.39
Rat (Chronic Oral)
1.45
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
489.6
Hydration Free Energy
-4.49
Log(D) at pH=7.4
1.59
Log(P)
0.46
Log S
-3.11
Log(Vapor Pressure)
-10.16
Melting Point
234.6
pKa Acid
6.65
pKa Basic
5.97
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 0.8670
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8670
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8300
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8300
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8050
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8050
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7820
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7820
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7726
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7726
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7258
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7258

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