Ent-18-acetoxy-3beta,7alpha-dihydroxykaur-15-en-17-al - Compound Card

Ent-18-acetoxy-3beta,7alpha-dihydroxykaur-15-en-17-al

Select a section from the left sidebar

Ent-18-acetoxy-3beta,7alpha-dihydroxykaur-15-en-17-al

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles O=CC1=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/C22H32O5/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/h10-11,14,16-19,25-26H,4-9,12H2,1-3H3/t14-,16?,17?,18-,19+,20+,21-,22-/m1/s1
InChIKey IIOXAOGAOJDHDX-ZVIJCYGTSA-N
Formula C22H32O5
HBA 5
HBD 2
MW 376.49
Rotatable Bonds 3
TPSA 83.83
LogP 2.64
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.82
Exact Mass 376.22
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: 163079020

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 376.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.57
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.16

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
52.27
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
11.62
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.04
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.0
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.18
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-7.57
Rat (Acute)
6.23
Rat (Chronic Oral)
1.77
Fathead Minnow
3.93
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
438.09
Hydration Free Energy
-4.87
Log(D) at pH=7.4
2.37
Log(P)
2.28
Log S
-3.5
Log(Vapor Pressure)
-7.3
Melting Point
153.19
pKa Acid
7.01
pKa Basic
5.46
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 0.9292
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9292
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8479
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8479
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8089
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8089
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7686
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7686
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7494
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7494
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7420
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7420
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7419
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7419
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7331
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7331
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7102
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7102

Download SDF