Ent-18-acetoxykaur-16-en-3,7-dione - Compound Card

Ent-18-acetoxykaur-16-en-3,7-dione

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Ent-18-acetoxykaur-16-en-3,7-dione

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles CC(=O)OC[C@@]1(C)C(=O)CC[C@@]2(C1CC(=O)[C@@]13C2CC[C@H](C3)C(=C)C1)C
InChI InChI=1S/C22H30O4/c1-13-10-22-11-15(13)5-6-16(22)20(3)8-7-18(24)21(4,12-26-14(2)23)17(20)9-19(22)25/h15-17H,1,5-12H2,2-4H3/t15-,16?,17?,20+,21-,22+/m1/s1
InChIKey LUHBOTKDTDNYKX-NOJNMJOFSA-N
Formula C22H30O4
HBA 4
HBD 0
MW 358.48
Rotatable Bonds 2
TPSA 60.44
LogP 3.88
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.77
Exact Mass 358.21
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: 162817166
Nmrshiftdb2: 70041768

No compound-protein relationship available.

Structure

SMILES: C=C(C1)C(C2)CCC(C123)C4C(CC3=O)CC(=O)CC4

Level: 0

Mol. Weight: 358.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.51
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.62
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.28
Plasma Protein Binding
70.49
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
14.67
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.22
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.11
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.08
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
-6.73
Rat (Acute)
2.04
Rat (Chronic Oral)
1.7
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
418.03
Hydration Free Energy
-5.61
Log(D) at pH=7.4
2.75
Log(P)
2.89
Log S
-4.2
Log(Vapor Pressure)
-6.84
Melting Point
135.32
pKa Acid
8.75
pKa Basic
4.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9292
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9292
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9255
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9255
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8842
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8842
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8653
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8653
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8332
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8332
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8025
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8025
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7872
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7872
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7817
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7817
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7752
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7752
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7609
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7609
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7529
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7529
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7517
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7517
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7477
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7477
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7375
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7375
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7369
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7369
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7349
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7349
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7250
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7250
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7234
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7234
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7234
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7234
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7184
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7184
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7167
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7167
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7139
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7139
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7124
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7124
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7050
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7050
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7048
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7048
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7042
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7042
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7017
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7017

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