5beta,9beta-dihydroxy-1-oxo-germacra-1(10),4(15)-dien-12,6-olide - Compound Card

5beta,9beta-dihydroxy-1-oxo-germacra-1(10),4(15)-dien-12,6-olide

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5beta,9beta-dihydroxy-1-oxo-germacra-1(10),4(15)-dien-12,6-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC1C(=C)CCC(=O)C(=C)C([C@@H](C2[C@@H]1OC(=O)[C@H]2C)O)O
InChI InChI=1S/C15H20O6/c1-6-4-5-9(16)7(2)12(18)13(19)10-8(3)15(20)21-14(10)11(6)17/h8,10-14,17-19H,1-2,4-5H2,3H3/t8-,10?,11?,12?,13+,14-/m0/s1
InChIKey CWNCZRPLWFIYST-CAAMUIISSA-N
Formula C15H20O6
HBA 6
HBD 3
MW 296.32
Rotatable Bonds 0
TPSA 104.06
LogP -0.28
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 296.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia herba-alba Asteraceae Plantae 72329

Showing of synonyms

  • Ahmed AA, Abou-El-Ela M, et al. (1990). Eudesmanolides and other constituents from Artemisia herba-alba.. Phytochemistry,1990,29(11),3661-3663. [View]
Pubchem: 162956610
Nmrshiftdb2: 60046257

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 296.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.88
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.53
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.44
Plasma Protein Binding
37.32
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
3.86
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.52
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.03
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.39
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1.32
Rat (Acute)
3.18
Rat (Chronic Oral)
2.76
Fathead Minnow
3.91
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
368.8
Hydration Free Energy
-14.78
Log(D) at pH=7.4
-0.12
Log(P)
-1.25
Log S
-1.12
Log(Vapor Pressure)
-8.87
Melting Point
164.59
pKa Acid
5.88
pKa Basic
5.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8630
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8630
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8513
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8513
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8316
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8316
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7917
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7917
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7689
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7689
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7173
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7173
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.7148
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.7148
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7106
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7106
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7013
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7013

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