15-hydroxy-8-alpha-(3'-hydroxy-isobutanoyloxy)-elemane-1,3,11(13)-trien-12,6-olide - Compound Card

15-hydroxy-8-alpha-(3'-hydroxy-isobutanoyloxy)-elemane-1,3,11(13)-trien-12,6-olide

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15-hydroxy-8-alpha-(3'-hydroxy-isobutanoyloxy)-elemane-1,3,11(13)-trien-12,6-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC(=C)[C@H]1[C@H](C=C)C[C@@H](C2[C@@H]1OC(=O)C2=C)OC(=O)C(CO)C
InChI InChI=1S/C18H24O6/c1-5-12-6-13(23-17(21)10(3)8-20)15-11(4)18(22)24-16(15)14(12)9(2)7-19/h5,10,12-16,19-20H,1-2,4,6-8H2,3H3/t10?,12-,13+,14+,15?,16-/m1/s1
InChIKey BMCYCYSQXCKZRX-PGUIMBBPSA-N
Formula C18H24O6
HBA 6
HBD 2
MW 336.38
Rotatable Bonds 6
TPSA 93.06
LogP 0.99
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 336.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Onopordon ambiguum Asteraceae Plantae —

Showing of synonyms

  • El-Moghazy SA, Ahmed AA, et al. (2002). A new eudesmane derivative from Onopordon ambiguum. Fitoterapia,2002,73,97-98. [View] [PubMed]
Pubchem: 162878592

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CCCC2

Level: 0

Mol. Weight: 336.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.650
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.500
Plasma Protein Binding
47.77
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.340
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.290
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.300
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.170
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
-0.410
Rat (Acute)
3.840
Rat (Chronic Oral)
2.210
Fathead Minnow
3.920
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
369.950
Hydration Free Energy
-9.350
Log(D) at pH=7.4
0.790
Log(P)
0.81
Log S
-2.62
Log(Vapor Pressure)
-7.69
Melting Point
99.37
pKa Acid
7.3
pKa Basic
4.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9355
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9355
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8470
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8470
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8255
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8255
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8216
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8216
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.7862
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.7862
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7564
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7564
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7522
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7522
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7328
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7328
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7287
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7287
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7171
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7171
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7067
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7067
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7033
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7033

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