1alpha,3beta-dihydroxy-7alpha,11alpha-germacra-4E,10(14)-dien-12,6alpha-olide - Compound Card

1alpha,3beta-dihydroxy-7alpha,11alpha-germacra-4E,10(14)-dien-12,6alpha-olide

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1alpha,3beta-dihydroxy-7alpha,11alpha-germacra-4E,10(14)-dien-12,6alpha-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C1O[C@H]2[C@H]([C@@H]1C)CCC(=C)[C@H](C[C@@H](/C(=C/2)/C)O)O
InChI InChI=1S/C15H22O4/c1-8-4-5-11-10(3)15(18)19-14(11)6-9(2)13(17)7-12(8)16/h6,10-14,16-17H,1,4-5,7H2,2-3H3/b9-6+/t10-,11-,12-,13-,14+/m0/s1
InChIKey LLPYDSMSNNUQCD-VIRWYYHKSA-N
Formula C15H22O4
HBA 4
HBD 2
MW 266.34
Rotatable Bonds 0
TPSA 66.76
LogP 1.57
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 266.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pyrethrum santolinoides Asteraceae-Compositae Plantae 2072400
2 Tanacetum sinaicum Asteraceae-Compositae Plantae —

Showing of synonyms

  • Mahmoud AA, Ahmed AA, et al. (1994). 2,3-secogermacranolides and germacranolides from Pyrethrum santolionoides. Phytochemistry,1994,36(2),393-398. [View]
  • Hegazy MEF, Hamed AR, et al. (2015). Anti-inflammatory sesquiterpenes from the medicinal herb Tanacetum sinaicum. RSC Advances,2015,5,44895-44901. [View]
Pubchem: 184464

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 266.34 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.91
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.21
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
38.3
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
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
5.79
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.41
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.12
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.57
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
-2.65
Rat (Acute)
2.54
Rat (Chronic Oral)
2.07
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
354.07
Hydration Free Energy
-10.32
Log(D) at pH=7.4
0.4
Log(P)
1.03
Log S
-1.71
Log(Vapor Pressure)
-6.75
Melting Point
151.74
pKa Acid
8.93
pKa Basic
5.71
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9152
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9152
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8488
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8488
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8474
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8474
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8464
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8464
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.8317
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.8317
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8270
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8270
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8056
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8056
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7959
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7959
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7699
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7699
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7622
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7622
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7603
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7603
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7499
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7499
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7474
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7474
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7471
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7471
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7435
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7435
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7424
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7424
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7406
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7406
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7388
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7388
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7331
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7331
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7307
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7307
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7301
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7301
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7192
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7192
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7190
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7190
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7168
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7168
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7132
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7132
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7119
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7119
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7111
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7111
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7086
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7086
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7067
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7067

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