5,6,11,14,17(R)-pentaacetoxy-3-benzoyloxy-15-hydroxysegetan-9-one - Compound Card

5,6,11,14,17(R)-pentaacetoxy-3-benzoyloxy-15-hydroxysegetan-9-one

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5,6,11,14,17(R)-pentaacetoxy-3-benzoyloxy-15-hydroxysegetan-9-one

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles CC(=O)O[C@@H]1[C@H]2[C@@H](Oc3ccccc3)[C@H](C[C@]2(O)C([C@@]2(C([C@@]1(OC(=O)C)CC1=C2[C@@H](C(C1=O)(C)C)OC(=O)C)OC(=O)C)C)OC(=O)C)C
InChI InChI=1S/C36H44O13/c1-17-15-35(43)26(27(17)48-23-13-11-10-12-14-23)30(45-19(3)38)36(49-22(6)41)16-24-25(29(44-18(2)37)33(7,8)28(24)42)34(9,31(35)46-20(4)39)32(36)47-21(5)40/h10-14,17,26-27,29-32,43H,15-16H2,1-9H3/t17-,26+,27-,29-,30+,31?,32?,34+,35+,36+/m0/s1
InChIKey WYKPBBZNSCLSTQ-YYMYQQQLSA-N
Formula C36H44O13
HBA 13
HBD 1
MW 684.74
Rotatable Bonds 7
TPSA 178.03
LogP 3.18
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 49
Formal Charge 0
Fraction CSP3 0.61
Exact Mass 684.28
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: 162817229
Nmrshiftdb2: 70049096

No compound-protein relationship available.

Structure

SMILES: O=C1CCC(=C12)C3CC(C2)CC4C(C3)CCC4Oc5ccccc5

Level: 1

Mol. Weight: 684.74 g/mol

Structure

SMILES: O=C1CCC(=C12)C3CC(C2)CC4C(C3)CCC4

Level: 0

Mol. Weight: 684.74 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 684.74 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.18
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
63.22

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.48
Plasma Protein Binding
94.42
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
9.83
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.61
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.87
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.73
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
-119362.62
Rat (Acute)
4.14
Rat (Chronic Oral)
2.97
Fathead Minnow
165.07
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
8058.28
Hydration Free Energy
-2.92
Log(D) at pH=7.4
1.96
Log(P)
3.29
Log S
-4.48
Log(Vapor Pressure)
-302.59
Melting Point
219.0
pKa Acid
6.53
pKa Basic
-0.94
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 0.9725
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9725
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7984
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7984
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7098
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7098
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7067
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7067

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