Ammolactone-A - Compound Card

Ammolactone-A

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Ammolactone-A

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpenoid
Canonical Smiles CCC(C(=O)O[C@@H]1C[C@@](C)(O)[C@H]2[C@@H]([C@@H]3[C@H]1C(C)C(=O)O3)C(=CC2)C)C
InChI InChI=1S/C20H30O5/c1-6-10(2)18(21)24-14-9-20(5,23)13-8-7-11(3)15(13)17-16(14)12(4)19(22)25-17/h7,10,12-17,23H,6,8-9H2,1-5H3/t10?,12?,13-,14-,15+,16+,17-,20-/m1/s1
InChIKey AQCWDMYAXGZHOF-ZDIJCOFXSA-N
Formula C20H30O5
HBA 5
HBD 1
MW 350.46
Rotatable Bonds 3
TPSA 72.83
LogP 2.86
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 350.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ammodaucus leucotrichus Apiaceae Plantae 79158

Showing of synonyms

  • Muckensturm B, Diyani F, et al. (1997). Ammolactone, a guaianolide from a medicinal plant, Ammodaucus leucotrichus. Phytochemistry,1997,44(5),907-910. [View]
Pubchem: 102065500

No compound-protein relationship available.

Structure

SMILES: O=C(O1)CC(C1C23)CCCC3CC=C2

Level: 0

Mol. Weight: 350.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.51
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.65
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.66
Plasma Protein Binding
55.5
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.47
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.4
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.25
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.32
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
-1.14
Rat (Acute)
2.97
Rat (Chronic Oral)
1.75
Fathead Minnow
3.92
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
377.48
Hydration Free Energy
-5.7
Log(D) at pH=7.4
2.09
Log(P)
3.01
Log S
-3.86
Log(Vapor Pressure)
-6.61
Melting Point
127.55
pKa Acid
9.83
pKa Basic
5.79
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9038
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9038
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8968
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8968
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8291
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8291
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8047
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8047
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7946
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7946
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7944
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7944
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7922
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7922
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7809
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7809
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7533
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7533
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7487
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7487
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7484
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7484
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7428
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7428
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7422
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7422
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7354
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7354
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7328
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7328
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7311
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7311
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7250
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7250
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7233
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7233
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7224
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7224
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7205
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7205
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7184
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7184
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7149
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7149
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7124
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7124
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7079
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7079
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7032
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7032
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7008
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7008

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