8alpha-hydroxy-1beta,10alpha-epoxygermacra-4,11(13)-dien-6alpha,12-olide - Compound Card

8alpha-hydroxy-1beta,10alpha-epoxygermacra-4,11(13)-dien-6alpha,12-olide

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8alpha-hydroxy-1beta,10alpha-epoxygermacra-4,11(13)-dien-6alpha,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(=C)[C@@H]2[C@H](C[C@]2([C@@H](CC1)O2)C)O
InChI InChI=1S/C15H20O4/c1-8-4-5-12-15(3,19-12)7-10(16)13-9(2)14(17)18-11(13)6-8/h6,10-13,16H,2,4-5,7H2,1,3H3/b8-6+/t10-,11+,12+,13+,15-/m0/s1
InChIKey SYSSJSZLJSTGFH-YYNDJATHSA-N
Formula C15H20O4
HBA 4
HBD 1
MW 264.32
Rotatable Bonds 0
TPSA 59.06
LogP 1.73
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 Brocchia cinerea Asteraceae Plantae 282208
2 Cotula cinerea Asteraceae Plantae —

Showing of synonyms

  • Jakupovic J, Aal MA, et al. (1988). Further glaucolides and other sesquiterpene lactones from Brocchia cinerea.. Phytochemistry,1988,27(7),2219-2224. [View]
  • Metwally MA, El-dahmy S, et al. (1986). Glaucolide-like sesquiterpene lactones from Cotula cinerea. Phytochemistry,1986,25(1),255-257. [View]
Pubchem: 163007130

No compound-protein relationship available.

Structure

SMILES: O=C(O1)C(=C)C(CC2)C1C=CCCC(O3)C23

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.16
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.41
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.18
Plasma Protein Binding
19.62
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
14.9
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.39
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.56
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.91
Micronucleos
Toxic
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
0.26
Rat (Acute)
3.45
Rat (Chronic Oral)
1.83
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
342.14
Hydration Free Energy
-7.53
Log(D) at pH=7.4
0.79
Log(P)
0.95
Log S
-2.12
Log(Vapor Pressure)
-5.42
Melting Point
102.91
pKa Acid
5.98
pKa Basic
3.76
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 0.8611
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8611
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7821
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7821
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7790
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7790
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7648
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7648
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7364
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7364
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7361
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7361
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7360
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7360
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7354
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7354
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7348
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7348
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7303
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7303
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7244
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7244
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7220
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7220
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7194
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7194
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7147
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7147
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7115
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7115

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