Ent-3beta,7alpha,17,18-tetracetoxy-15beta,16beta-epoxykaurane - Compound Card

Ent-3beta,7alpha,17,18-tetracetoxy-15beta,16beta-epoxykaurane

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Ent-3beta,7alpha,17,18-tetracetoxy-15beta,16beta-epoxykaurane

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles CC(=O)OC[C@@]1(C)[C@@H](CC[C@@]2(C1C[C@H](OC(=O)C)[C@]13C2CC[C@H](C1)[C@]1([C@@H]3O1)COC(=O)C)C)OC(=O)C
InChI InChI=1S/C28H40O9/c1-15(29)33-13-26(6)21-11-23(36-18(4)32)27-12-19(28(24(27)37-28)14-34-16(2)30)7-8-20(27)25(21,5)10-9-22(26)35-17(3)31/h19-24H,7-14H2,1-6H3/t19-,20?,21?,22-,23+,24-,25+,26-,27-,28+/m1/s1
InChIKey OFFATORNHROHHC-ZFLKZFMKSA-N
Formula C28H40O9
HBA 9
HBD 0
MW 520.62
Rotatable Bonds 6
TPSA 117.73
LogP 3.36
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 520.27
Number of Lipinski Rule Violations 1
# 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: 162817165
Nmrshiftdb2: 70041772

No compound-protein relationship available.

Structure

SMILES: C123C4C(O4)C(C1)CCC2C5C(CC3)CCCC5

Level: 0

Mol. Weight: 520.62 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.05
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.78
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.06

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.42
Plasma Protein Binding
58.64
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
11.46
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.34
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.16
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.33
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
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
-903.8
Rat (Acute)
3.15
Rat (Chronic Oral)
2.15
Fathead Minnow
4.84
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
459.47
Hydration Free Energy
-2.83
Log(D) at pH=7.4
3.13
Log(P)
2.22
Log S
-5.03
Log(Vapor Pressure)
-8.07
Melting Point
144.54
pKa Acid
8.22
pKa Basic
3.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7614
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7614
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7216
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7216
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7190
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7190
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7130
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7130

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