(1R,2S,5S,6S,9S,10R)-5,9,10-trimethyl-3-oxatetracyclo[7.4.0.01,10.02,6]tridec-12-ene-4,11-dione - Compound Card

(1R,2S,5S,6S,9S,10R)-5,9,10-trimethyl-3-oxatetracyclo[7.4.0.01,10.02,6]tridec-12-ene-4,11-dione

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(1R,2S,5S,6S,9S,10R)-5,9,10-trimethyl-3-oxatetracyclo[7.4.0.01,10.02,6]tridec-12-ene-4,11-dione

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C[C@@H]1C(=O)O[C@H]2[C@H]1CC[C@]1([C@]32C=CC(=O)[C@]13C)C
InChI InChI=1S/C15H18O3/c1-8-9-4-6-13(2)14(3)10(16)5-7-15(13,14)11(9)18-12(8)17/h5,7-9,11H,4,6H2,1-3H3/t8-,9-,11-,13+,14+,15+/m0/s1
InChIKey DAGAGXCQQYCLAE-DZOXWOQYSA-N
Formula C15H18O3
HBA 3
HBD 0
MW 246.31
Rotatable Bonds 0
TPSA 43.37
LogP 2.11
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 246.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia hugueti Asteraceae Plantae 4219

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones from North African Artemisia species.. Phytochemistry,1994,37(2),477-485. [View]
Pubchem: 101596929
Nmrshiftdb2: 60046263

No compound-protein relationship available.

Structure

SMILES: C1=CC(=O)C(C123)C2CCC4C3OC(=O)C4

Level: 0

Mol. Weight: 246.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.46
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.67
Plasma Protein Binding
52.81
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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.2
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.31
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.04
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.51
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.08
Rat (Acute)
2.15
Rat (Chronic Oral)
1.57
Fathead Minnow
3.87
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
333.98
Hydration Free Energy
-5.32
Log(D) at pH=7.4
1.71
Log(P)
1.54
Log S
-2.61
Log(Vapor Pressure)
-4.22
Melting Point
192.58
pKa Acid
8.77
pKa Basic
6.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8804
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8804
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8561
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8561
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8481
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8481
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8156
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8156
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8038
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8038
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7779
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7779
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7778
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7778
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7702
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7702
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7622
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7622
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7476
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7476
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7398
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7398
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7370
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7370
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7317
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7317
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7289
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7289
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7254
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7254
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7210
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7210
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7075
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7075

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