(1R,2R,3aR,5S,10S,11S,13R,13aS)-3a,11,13-tris(acetyloxy)-2-hydroxy-2,5,8,8-tetramethyl-12-methylidene-10-(2-methylpropoxy)-4,9-dioxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl acetate - Compound Card

(1R,2R,3aR,5S,10S,11S,13R,13aS)-3a,11,13-tris(acetyloxy)-2-hydroxy-2,5,8,8-tetramethyl-12-methylidene-10-(2-methylpropoxy)-4,9-dioxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl acetate

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(1R,2R,3aR,5S,10S,11S,13R,13aS)-3a,11,13-tris(acetyloxy)-2-hydroxy-2,5,8,8-tetramethyl-12-methylidene-10-(2-methylpropoxy)-4,9-dioxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl acetate

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles CC(CO[C@@H]1[C@@H](OC(=O)C)C(=C)[C@H](OC(=O)C)[C@H]2[C@@H](OC(=O)C)[C@H](C[C@]2(OC(=O)C)C(=O)[C@H](/C=C/C(C1=O)(C)C)C)C)C
InChI InChI=1S/C32H46O11/c1-16(2)15-39-28-27(42-22(8)35)19(5)26(41-21(7)34)24-25(40-20(6)33)18(4)14-32(24,43-23(9)36)29(37)17(3)12-13-31(10,11)30(28)38/h12-13,16-18,24-28H,5,14-15H2,1-4,6-11H3/b13-12+/t17-,18-,24+,25-,26-,27-,28+,32+/m0/s1
InChIKey JAZNJEUTUCVTMK-AKVYQBFCSA-N
Formula C32H46O11
HBA 11
HBD 0
MW 606.71
Rotatable Bonds 7
TPSA 148.57
LogP 3.71
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.69
Exact Mass 606.3
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia paralias Euphorbiaceae Plantae 756629

Showing of synonyms

  • Abdelgaleil SAM, Kassem SMI, et al. (2001). Diterpenoids from Euphorbia paralias. Phytochemistry,2001,58,1135-1139. [View] [PubMed]
Pubchem: 5275797

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CC(=C)CCC(=O)CC=CCC2=O

Level: 0

Mol. Weight: 606.71 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
90.77
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.87
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.02
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.29
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.26
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-3231.15
Rat (Acute)
2.93
Rat (Chronic Oral)
2.42
Fathead Minnow
14.08
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
393.83
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.41
Log(P)
3.19
Log S
-4.52
Log(Vapor Pressure)
-8.87
Melting Point
153.43
pKa Acid
6.57
pKa Basic
1.08
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8146
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8146
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7468
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7468
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7357
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7357

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