1beta-hydroxy-6betaH,7alphaH,11alphaH-germacran-4(5),10(15)-dien-6,12-olide - Compound Card

1beta-hydroxy-6betaH,7alphaH,11alphaH-germacran-4(5),10(15)-dien-6,12-olide

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1beta-hydroxy-6betaH,7alphaH,11alphaH-germacran-4(5),10(15)-dien-6,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C/1=C\[C@H]2OC(=O)[C@@H](C2CCC(=C)C(CC1)O)C
InChI InChI=1S/C15H22O3/c1-9-4-7-13(16)10(2)5-6-12-11(3)15(17)18-14(12)8-9/h8,11-14,16H,2,4-7H2,1,3H3/b9-8+/t11-,12?,13?,14-/m1/s1
InChIKey LEXBBZCFWJNTGC-QTUMPXBJSA-N
Formula C15H22O3
HBA 3
HBD 1
MW 250.34
Rotatable Bonds 0
TPSA 46.53
LogP 2.6
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 250.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia herba-alba Asteraceae Plantae 72329

Showing of synonyms

  • Gordon MM, Van Derveer D, et al. (1981). New germacranolides from Artemisia herba alba. X-ray crystal structures of 3beta,8alpha-dihydroxy-6betaH,7alphaH,11betaH-germacran-4(14),9(10)-dien-6,12-olide and the corresponding 3-oxo-olide.. Journal of Natural Products,1981,44(4),432-440. [View]
Pubchem: 162940242

No compound-protein relationship available.

Structure

SMILES: C1CC(=C)CCCC=CC(C12)OC(=O)C2

Level: 0

Mol. Weight: 250.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.22
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
41.23
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.07
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.25
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.33
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.01
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
0.31
Rat (Acute)
2.06
Rat (Chronic Oral)
1.88
Fathead Minnow
4.12
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
330.27
Hydration Free Energy
-6.39
Log(D) at pH=7.4
1.35
Log(P)
2.23
Log S
-2.61
Log(Vapor Pressure)
-5.16
Melting Point
93.69
pKa Acid
10.28
pKa Basic
6.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9067
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9067
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9021
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9021
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8874
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8874
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7881
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7881
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7843
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7843
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7635
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7635
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7571
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7571
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7547
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7547
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7484
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7484
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7465
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7465
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7413
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7413
Vitamin D3 receptor A Q9PTN2 VDRA_DANRE Danio rerio 3 0.7341
Vitamin D3 receptor A Q9PTN2 VDRA_DANRE Danio rerio 3 0.7341
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7330
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7330
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7300
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7300
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7242
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7242
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7209
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7209
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7202
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7202
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7186
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7186
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7182
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7182
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7160
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7160
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7135
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7135
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7130
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7130
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7101
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7101
Vitamin D3 receptor P11473 VDR_HUMAN Homo sapiens 3 0.7032
Vitamin D3 receptor P11473 VDR_HUMAN Homo sapiens 3 0.7032
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7020
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7020
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7014
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7014

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