11,12-dihydroxy-7-oxo-ent-abieta-8,11,13-trien-16-oic acid methyl ester - Compound Card

11,12-dihydroxy-7-oxo-ent-abieta-8,11,13-trien-16-oic acid methyl ester

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11,12-dihydroxy-7-oxo-ent-abieta-8,11,13-trien-16-oic acid methyl ester

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles CC(=O)OCC(c1cc2C(=O)C[C@H]3[C@@](c2c(c1O)O)(C)CCCC3(C)C)C
InChI InChI=1S/C22H30O5/c1-12(11-27-13(2)23)14-9-15-16(24)10-17-21(3,4)7-6-8-22(17,5)18(15)20(26)19(14)25/h9,12,17,25-26H,6-8,10-11H2,1-5H3/t12?,17-,22-/m1/s1
InChIKey CJYNUSAOAPXPPP-OJNPPMJPSA-N
Formula C22H30O5
HBA 5
HBD 2
MW 374.48
Rotatable Bonds 3
TPSA 83.83
LogP 4.43
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 374.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia guyoniana Euphorbiaceae Plantae 1138347

Showing of synonyms

  • Haba H, Marcourt L, et al. (2013). Minor ent-abietane diterpenoids from Euphorbia guyoniana. Natural Products Communications,2013,8(11),1519-1522. [View] [PubMed]
Pubchem: 162904861
Nmrshiftdb2: 70036686

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C3C(CC2=O)CCCC3

Level: 0

Mol. Weight: 374.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.72
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.89
Plasma Protein Binding
87.11
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
17.18
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.64
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.19
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.57
Micronucleos
Toxic
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
-0.4
Rat (Acute)
2.28
Rat (Chronic Oral)
2.53
Fathead Minnow
4.03
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
405.24
Hydration Free Energy
-7.96
Log(D) at pH=7.4
3.03
Log(P)
3.7
Log S
-4.74
Log(Vapor Pressure)
-7.52
Melting Point
160.46
pKa Acid
7.31
pKa Basic
5.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8219
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8219
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7789
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7789
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7339
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7339
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7283
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7283
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7181
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7181
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7177
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7177
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7138
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7138
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7057
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7057
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7016
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7016

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