13-hydroxy-3-oxogermacra-1(10),7(12)-6alpha,12-olide - Compound Card

13-hydroxy-3-oxogermacra-1(10),7(12)-6alpha,12-olide

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13-hydroxy-3-oxogermacra-1(10),7(12)-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC1=C2CC/C(=C/CC(=O)[C@@H](C[C@H]2OC1=O)C)/C
InChI InChI=1S/C15H20O4/c1-9-3-5-11-12(8-16)15(18)19-14(11)7-10(2)13(17)6-4-9/h4,10,14,16H,3,5-8H2,1-2H3/b9-4+/t10-,14-/m1/s1
InChIKey DPKLHUJIQNJYBQ-MJNWLPMTSA-N
Formula C15H20O4
HBA 4
HBD 1
MW 264.32
Rotatable Bonds 1
TPSA 63.6
LogP 1.93
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 reptans Asteraceae Plantae 72350

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones and acetylenes from Artemisia reptans.. Phytochemistry,1994,37(4),1055-1099. [View]
Pubchem: 14543463
Nmrshiftdb2: 60079528

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C=12)CCC(=O)CC=CCC2

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
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
-2.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.47
Plasma Protein Binding
46.28
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
5.12
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.58
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.2
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.5
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
0.05
Rat (Acute)
2.27
Rat (Chronic Oral)
2.03
Fathead Minnow
4.14
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
341.1
Hydration Free Energy
-9.28
Log(D) at pH=7.4
1.02
Log(P)
1.49
Log S
-2.29
Log(Vapor Pressure)
-5.57
Melting Point
115.56
pKa Acid
8.53
pKa Basic
5.02
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.9477
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.9477
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9216
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9216
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8707
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8707
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8657
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8657
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8564
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8564
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8149
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8149
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8122
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8122
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7858
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7858
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7695
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7695
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7673
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7673
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7552
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7552
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7351
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7351
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7258
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7258
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7220
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7220
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7165
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7165
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7117
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7117
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7048
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7048
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7025
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7025

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