Naupliolide - Compound Card

Naupliolide

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Naupliolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C1O[C@H]2[C@H]3[C@@H]1CCC=C(C(=O)[C@@H]3[C@H]1[C@]2(C)C1)C
InChI InChI=1S/C15H18O3/c1-7-4-3-5-8-10-11(12(7)16)9-6-15(9,2)13(10)18-14(8)17/h4,8-11,13H,3,5-6H2,1-2H3/t8-,9-,10-,11+,13-,15-/m0/s1
InChIKey DTEGLWIVCXHONU-MBVZUPLLSA-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 Nauplius graveolens Asteraceae Plantae 73976

Showing of synonyms

  • Akssira M, Mellouki F, et al. (2006). Naupliolide, a sesquiterpene lactone with a novel tetracyclic skeleton from Nauplius graveolens subsp. Odorus. Tetrahedron Letters,2006,47,6719-6721. [View]
Pubchem: 101404203
Nmrshiftdb2: 70080327

No compound-protein relationship available.

Structure

SMILES: C12C(C1)C3C4C2C(=O)C=CCCC4C(=O)O3

Level: 0

Mol. Weight: 246.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.49
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.15

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.83
Plasma Protein Binding
53.99
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
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
13.08
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.01
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.28
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.11
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
1.1
Rat (Acute)
2.03
Rat (Chronic Oral)
1.84
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
354.23
Hydration Free Energy
-5.15
Log(D) at pH=7.4
1.8
Log(P)
1.75
Log S
-2.79
Log(Vapor Pressure)
-5.22
Melting Point
179.16
pKa Acid
9.28
pKa Basic
5.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8631
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8631
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8282
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8282
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7841
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7841
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7660
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7660
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7647
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7647
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7645
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7645
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7612
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7612
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7582
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7582
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7458
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7458
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7317
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7317
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7213
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7213
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7144
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7144
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7118
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7118
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7096
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7096
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7043
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7043
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7034
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7034

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