1-oxo-9beta-hydroxygermacra-4,10(14)-dien-6beta,11betaH-12,6-olide - Compound Card

1-oxo-9beta-hydroxygermacra-4,10(14)-dien-6beta,11betaH-12,6-olide

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1-oxo-9beta-hydroxygermacra-4,10(14)-dien-6beta,11betaH-12,6-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](C2C[C@@H](C(=C)C(=O)CC1)O)C
InChI InChI=1S/C15H20O4/c1-8-4-5-12(16)10(3)13(17)7-11-9(2)15(18)19-14(11)6-8/h6,9,11,13-14,17H,3-5,7H2,1-2H3/b8-6+/t9-,11?,13-,14+/m0/s1
InChIKey TWDWHZLPWNJPES-VMFLAXQGSA-N
Formula C15H20O4
HBA 4
HBD 1
MW 264.32
Rotatable Bonds 0
TPSA 63.6
LogP 1.78
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia herba-alba Asteraceae Plantae 72329

Showing of synonyms

  • Mako JA, Sanz-Cervera JF, et al. (1994). New germacranolides and eudesmanolides from North African Artemisia herba-alba.. Journal of Natural Products,1994,57(7),939-946. [View]
Pubchem: 162919972
Nmrshiftdb2: 60074962

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.41
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.48
Plasma Protein Binding
41.64
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
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
6.72
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.3
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.52
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.33
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
0.25
Rat (Acute)
3.07
Rat (Chronic Oral)
2.04
Fathead Minnow
4.01
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
336.08
Hydration Free Energy
-8.59
Log(D) at pH=7.4
0.72
Log(P)
0.63
Log S
-1.79
Log(Vapor Pressure)
-6.11
Melting Point
124.94
pKa Acid
8.98
pKa Basic
5.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.8715
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.8715
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8536
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8536
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8381
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8381
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.8375
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.8375
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8209
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8209
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8200
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8200
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7688
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7688
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7656
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7656
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7557
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7557
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7360
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7360
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7289
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7289
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7174
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7174
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7158
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7158
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7108
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7108
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7084
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7084

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