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(1S,2S,3aR,4R,5S,10R,12R,13S,13aS)-4,10,13-tris(acetyloxy)-3a-hydroxy-2,5,8,8,12-pentamethyl-9-oxo-tetradecahydro-1H-cyclopenta[12]annulen-1-yl benzoate

Family: Plantae - Euphorbiaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Diterpenoid

Canonical Smiles	CC(=O)O[C@@H]1[C@H]2[C@@H](OC(=O)c3ccccc3)[C@H](C[C@]2(O)[C@@H]([C@@]2([C@@]1(C)C[C@@]1([C@H]2CC(C1=O)(C)C)OC(=O)C)C)OC(=O)C)C
InChI	InChI=1S/C33H42O10/c1-17-14-32(39)23(24(17)42-26(37)21-12-10-9-11-13-21)25(40-18(2)34)30(7)16-33(43-20(4)36)22(15-29(5,6)27(33)38)31(30,8)28(32)41-19(3)35/h9-13,17,22-25,28,39H,14-16H2,1-8H3/t17-,22-,23+,24-,25+,28+,30-,31+,32+,33-/m0/s1
InChIKey	IEQTVHJLWRGNIY-ANWQMKQLSA-N
Formula	C₃₃H₄₂O₁₀
HBA	10
HBD	1
MW	598.69
Rotatable Bonds	5
TPSA	142.5
LogP	3.81
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.67
Exact Mass	598.28
Number of Lipinski Rule Violations	1

#	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: 390635

Cas: 210046-65-4

Gnps: CCMSLIB00000853264

Zinc: ZINC000005839381

Chembl: CHEMBL1964386

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC2CCC(C3)C2CC(C4)C3C(C45)CCC5=O

Level: 1

Mol. Weight: 598.69 g/mol

SMILES: O=C1CCC(C12)C3C(C2)CC4C(C3)CCC4

Level: 0

Mol. Weight: 598.69 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 598.69 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.99
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.55
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 2.2

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.55
Plasma Protein Binding: 103.91
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: Substrate
OATP1B1: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 8.24
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.25
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.56
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.69
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: -8332.81
Rat (Acute): 4.16
Rat (Chronic Oral): 2.72
Fathead Minnow: 24.16
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 360.82
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 2.95
Log(P): 4.51
Log S: -5.21
Log(Vapor Pressure): -12.43
Melting Point: 218.53
pKa Acid: 7.59
pKa Basic: 1.91

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7335
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7335

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