12-hydroxy-8,12-abietadiene-3,11,14-trione - Compound Card

12-hydroxy-8,12-abietadiene-3,11,14-trione

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12-hydroxy-8,12-abietadiene-3,11,14-trione

Structure
Zoomed Structure
  • Family: Plantae - Verbenaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Abietane Diterpenoid
Canonical Smiles O=C1C(=C(C(C)C)C(=O)C2=C1[C@@]1(C)CCC(=O)C([C@@H]1CC2)(C)C)O
InChI InChI=1S/C20H26O4/c1-10(2)14-16(22)11-6-7-12-19(3,4)13(21)8-9-20(12,5)15(11)18(24)17(14)23/h10,12,23H,6-9H2,1-5H3/t12-,20-/m0/s1
InChIKey PCCTZPOSLPXEHH-YUNKPMOVSA-N
Formula C20H26O4
HBA 4
HBD 1
MW 330.42
Rotatable Bonds 1
TPSA 71.44
LogP 3.71
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 330.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Clerodendrum eriophyllum Verbenaceae Plantae 54214

Showing of synonyms

  • Machumi F, Samoylenko V, et al. (2010). Antimicrobial and antiparasitic abietane diterpenoids from the roots of Clerodendrum eriophyllum. Natural Product Communication,2010,5(6),853-858. [View] [PubMed]
Pubchem: 101667557

No compound-protein relationship available.

Structure

SMILES: O=C1C=CC(=O)C(=C12)CCC3C2CCC(=O)C3

Level: 0

Mol. Weight: 330.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.44
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.620
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.050
Plasma Protein Binding
83.68
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
11.250
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.120
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.750
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.220
Micronucleos
Safe
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
Toxic
T. Pyriformis
1.680
Rat (Acute)
2.420
Rat (Chronic Oral)
2.010
Fathead Minnow
4.140
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
384.730
Hydration Free Energy
-7.190
Log(D) at pH=7.4
2.620
Log(P)
3.37
Log S
-3.86
Log(Vapor Pressure)
-6.58
Melting Point
179.03
pKa Acid
5.8
pKa Basic
1.27
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7360
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7360
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7341
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7341
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7046
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7046
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7003
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7003

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