8alpha-hydroxy-11alpha,13-dihydrozaluzanin C - Compound Card

8alpha-hydroxy-11alpha,13-dihydrozaluzanin C

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8alpha-hydroxy-11alpha,13-dihydrozaluzanin C

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O[C@H]1C[C@@H]2[C@H](C1=C)[C@H]1OC(=O)C(C1[C@H](CC2=C)O)C
InChI InChI=1S/C15H20O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h8-14,16-17H,1-2,4-5H2,3H3/t8?,9-,10-,11-,12-,13?,14+/m0/s1
InChIKey AEWOONBLAKEKSC-BBPNPORVSA-N
Formula C15H20O4
HBA 4
HBD 2
MW 264.32
Rotatable Bonds 0
TPSA 66.76
LogP 1.04
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea scoparia Asteraceae Plantae 2072395
2 Volutaria lippii Asteraceae Plantae 41663

Showing of synonyms

  • Helal AM, Nakamura N, et al. (1997). Guaianolides from Centaurea scoparia. Phytochemistry,1997,45(3),551-554. [View]
  • Rafrafi M, Ben Salah H, et al. (2021). Sesquiterpene lactones and flavonoids with chemotaxonomic significance from Volutaria lippii (L.) Cass. Biochemical Systematics and Ecology, 2021, 96, 104249. [View]
Pubchem: 101705725

No compound-protein relationship available.

Structure

SMILES: C=C1CCC2C(=C)CCC(C3C12)CC(=O)O3

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.34
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.57
Plasma Protein Binding
38.66
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.86
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
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.07
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.12
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
-1.37
Rat (Acute)
3.82
Rat (Chronic Oral)
1.73
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
357.38
Hydration Free Energy
-8.6
Log(D) at pH=7.4
0.2
Log(P)
0.6
Log S
-1.65
Log(Vapor Pressure)
-6.62
Melting Point
165.73
pKa Acid
7.81
pKa Basic
5.26
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 0.9005
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9005
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.8820
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.8820
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8685
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8685
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8638
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8638
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8504
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8504
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.8301
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.8301
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8164
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8164
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.8145
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.8145
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8118
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8118
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7798
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7798
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7720
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7720
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7715
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7715
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7684
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7684
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7664
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7664
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7554
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7554
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7545
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7545
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 4 0.7500
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 4 0.7500
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7402
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7402
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7387
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7387
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7360
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7360
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7345
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7345
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7342
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7342
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7328
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7328
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7314
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7314
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7298
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7298
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7166
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7166
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7162
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7162
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7141
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7141
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7097
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7097
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7089
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7089
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7049
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7049
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7042
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7042
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7029
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7029

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