Ent-18-acetoxy-3beta,7alpha,17-trihydroxykaur-15-ene - Compound Card

Ent-18-acetoxy-3beta,7alpha,17-trihydroxykaur-15-ene

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Ent-18-acetoxy-3beta,7alpha,17-trihydroxykaur-15-ene

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles OCC1=C[C@@]23C[C@H]1CCC3[C@]1(C(C[C@@H]2O)[C@@](C)(COC(=O)C)[C@@H](CC1)O)C
InChI InChI=1S/C22H34O5/c1-13(24)27-12-21(3)17-8-19(26)22-9-14(15(10-22)11-23)4-5-16(22)20(17,2)7-6-18(21)25/h10,14,16-19,23,25-26H,4-9,11-12H2,1-3H3/t14-,16?,17?,18-,19+,20+,21-,22-/m1/s1
InChIKey FRDLKANXGVGBKH-ZVIJCYGTSA-N
Formula C22H34O5
HBA 5
HBD 3
MW 378.51
Rotatable Bonds 3
TPSA 86.99
LogP 2.43
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 378.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sideritis moorei Lamiaceae Plantae 3394641

Showing of synonyms

  • Ghoumari H, Benajiba MH, et al. (2005). ent-Kauranoid derivatives from Sideritis moorei. Phytochemistry,2005,66(12),1492-1498. [View] [PubMed]
Pubchem: 163026999

No compound-protein relationship available.

Structure

SMILES: C1=CC(C2)CCC(C123)C4C(CC3)CCCC4

Level: 0

Mol. Weight: 378.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.7
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.71

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.55
Plasma Protein Binding
53.61
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
10.78
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.91
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.63
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.49
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
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
-8.3
Rat (Acute)
3.58
Rat (Chronic Oral)
2.24
Fathead Minnow
3.95
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
428.27
Hydration Free Energy
-5.3
Log(D) at pH=7.4
1.95
Log(P)
1.94
Log S
-3.29
Log(Vapor Pressure)
-7.54
Melting Point
163.78
pKa Acid
8.67
pKa Basic
5.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9050
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9050
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8510
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8510
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7993
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7993
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7836
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7836
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7714
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7714
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7667
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7667
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7626
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7626
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7527
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7527
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7490
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7490
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7409
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7409
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 4 0.7360
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 4 0.7360
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7337
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7337
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7314
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7314
Trichothecene 3-O-acetyltransferase O42692 O42692_GIBZA Gibberella zeae 4 0.7119
Trichothecene 3-O-acetyltransferase O42692 O42692_GIBZA Gibberella zeae 4 0.7119
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7038
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7038
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7024
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7024

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