3beta,14beta-dihydroxy-19-methoxy-5alpha-card-20(22)-enolide - Compound Card

3beta,14beta-dihydroxy-19-methoxy-5alpha-card-20(22)-enolide

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3beta,14beta-dihydroxy-19-methoxy-5alpha-card-20(22)-enolide

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Terpenoid
Canonical Smiles CO[C@H]1O[C@H]2C[C@@]31[C@@H](CC[C@@H]1[C@@H]3CC[C@]3([C@]1(O)CC[C@@H]3C1=CC(=O)OC1)C)C[C@H]2O
InChI InChI=1S/C24H34O6/c1-22-7-5-16-17(24(22,27)8-6-15(22)13-9-20(26)29-12-13)4-3-14-10-18(25)19-11-23(14,16)21(28-2)30-19/h9,14-19,21,25,27H,3-8,10-12H2,1-2H3/t14-,15+,16-,17+,18+,19-,21-,22+,23+,24-/m0/s1
InChIKey PSDNXUAVCZUOAL-KIBAJTNGSA-N
Formula C24H34O6
HBA 6
HBD 2
MW 418.53
Rotatable Bonds 2
TPSA 85.22
LogP 2.57
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.88
Exact Mass 418.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Calotropis procera Apocynaceae Plantae 141467

Showing of synonyms

  • Shaker KM, Morsy N, et al. (2010). Secondary metabolites from Calotropis procera (Aiton). Phytochemistry Letters,2010,3(4),212-216. [View]
Pubchem: 162929971
Nmrshiftdb2: 70016604

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)C=C1C(CC2)C(CC3)C2C(C3C456)CCC6CCC(C4)OC5

Level: 1

Mol. Weight: 418.53 g/mol

Structure

SMILES: C1CCC(CC2)C1C(C2C345)CCC5CCC(C3)OC4

Level: 0

Mol. Weight: 418.53 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 418.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.19

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.820
Plasma Protein Binding
58.13
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.740
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.820
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-2.310
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.500
Micronucleos
Safe
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
-69.790
Rat (Acute)
3.290
Rat (Chronic Oral)
1.870
Fathead Minnow
3.770
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
495.290
Hydration Free Energy
-3.270
Log(D) at pH=7.4
2.340
Log(P)
1.89
Log S
-4.04
Log(Vapor Pressure)
-8.83
Melting Point
228.67
pKa Acid
8.73
pKa Basic
7.05
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 0.8654
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8654
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.8228
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.8228
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8136
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8136
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7976
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7976
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7894
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7894
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7778
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7778
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7666
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7666
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7662
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7662
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7624
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7624
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7577
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7577
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7569
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7569
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7178
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7178

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