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

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

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Ent-3beta-acetoxy-7alpha,18-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)(CO)[C@@H](CC1)OC(=O)C)C
InChI InChI=1S/C22H32O5/c1-13(25)27-19-6-7-20(2)16-5-4-14-9-22(16,10-15(14)11-23)18(26)8-17(20)21(19,3)12-24/h10-11,14,16-19,24,26H,4-9,12H2,1-3H3/t14-,16?,17?,18+,19-,20+,21-,22-/m1/s1
InChIKey CLOLDMTTYQNMNE-QBUDDENOSA-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: 162998535

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)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.64
Plasma Protein Binding
51.56
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
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
11.64
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
-0.14
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.38
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Toxic
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-7.94
Rat (Acute)
5.75
Rat (Chronic Oral)
1.72
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
448.33
Hydration Free Energy
-5.6
Log(D) at pH=7.4
2.45
Log(P)
2.39
Log S
-3.81
Log(Vapor Pressure)
-7.61
Melting Point
150.25
pKa Acid
7.16
pKa Basic
6.66
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.9441
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.9441
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9243
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9243
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8008
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8008
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7849
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7849
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7656
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7656
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7111
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7111
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 4 0.7065
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 4 0.7065
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7063
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7063

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