Kaurenoic acid - Compound Card

Kaurenoic acid

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Kaurenoic acid

Structure
Zoomed Structure
  • Family: Plantae - Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpene
Canonical Smiles C=C1C[C@@]23C[C@H]1CC[C@H]3[C@]1([C@H](CC2)[C@@](C)(CCC1)C(=O)O)C
InChI InChI=1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)/t14-,15+,16+,18-,19-,20-/m1/s1
InChIKey NIKHGUQULKYIGE-OTCXFQBHSA-N
Formula C20H30O2
HBA 1
HBD 1
MW 302.46
Rotatable Bonds 1
TPSA 37.3
LogP 5.04
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 302.22
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Aspilia mossambicensis Asteraceae Plantae 1932724
2 Helichrysum foetidum Compositae Plantae 261783

Showing of synonyms

  • Page JE, Balza F, et al. (1992). Biologically active diterpenes from Aspilia mossambicensis, a chimpanzee medicinal plant.. Phytochemistry,1992,31(10),3437-3439. [View] [PubMed]
  • Malolo FA, Bissoue Nouga A, et al. (2015). Protease-inhibiting, molecular modeling and antimicrobial activities of extracts and constituents from Helichrysum foetidum and Helichrysum mechowianum (compositae).. Chemistry Central journal,2015, 9, 32. [View] [PubMed]
Pubchem: 73062
Kegg Ligand: C11874
Chebi: 15417
Nmrshiftdb2: 60027466
Metabolights: MTBLC15417
Pdb Ligand: NE4
Bindingdb: 50466103
CPRiL: 84585
Structure

SMILES: C=C(C1)C(C2)CCC(C123)C4C(CC3)CCCC4

Level: 0

Mol. Weight: 302.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.31

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.45
Plasma Protein Binding
83.68
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.37
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.03
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.45
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.81
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
-2.18
Rat (Acute)
2.4
Rat (Chronic Oral)
1.73
Fathead Minnow
3.76
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
365.45
Hydration Free Energy
-2.66
Log(D) at pH=7.4
2.77
Log(P)
4.97
Log S
-5.36
Log(Vapor Pressure)
-7.38
Melting Point
199.93
pKa Acid
5.61
pKa Basic
8.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.9568
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.9568
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8335
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8335
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.8188
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.8188
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8004
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8004
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7988
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7988
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7710
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7710
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7611
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7611
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7467
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7467
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7415
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7415
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7407
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7407
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7014
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7014

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