Xylopic acid - Compound Card

Xylopic acid

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Xylopic acid

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpene
Canonical Smiles CC(=O)O[C@@H]1C(=C)C2CC31CC[C@H]1C([C@@H]3CC2)(C)CCCC1(C)C(=O)O
InChI InChI=1S/C22H32O4/c1-13-15-6-7-17-20(3)9-5-10-21(4,19(24)25)16(20)8-11-22(17,12-15)18(13)26-14(2)23/h15-18H,1,5-12H2,2-4H3,(H,24,25)/t15?,16-,17-,18+,20?,21?,22?/m0/s1
InChIKey AQBQBBLJTDSVLC-LLQRNYNASA-N
Formula C22H32O4
HBA 3
HBD 1
MW 360.49
Rotatable Bonds 2
TPSA 63.6
LogP 4.58
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.82
Exact Mass 360.23
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Xylopia aethiopica Annonaceae Plantae 1317910
2 Zanthoxylum leprieurii Rutaceae Plantae 992815

Showing of synonyms

  • Soh D, Ernestine N, et al. (2022). Antiproliferative activity of semisynthetic xylopic acid derivatives.. Natural product research,2022, 36(5), 1288-1295. [View] [PubMed]
  • Guetchueng ST, Nahar L, et al. (2017). Kaurane diterpenes from the fruits of Zanthoxylum leprieurii (Rutaceae). Rec. Nat. Prod., (2017), 11(3) 304-309. [View]
Pubchem: 354614

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 360.49 g/mol

Antiproliferative

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.72
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.47
Plasma Protein Binding
73.45
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
2.95
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.13
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.25
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.22
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
-5.74
Rat (Acute)
2.44
Rat (Chronic Oral)
1.97
Fathead Minnow
3.96
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
402.7
Hydration Free Energy
-3.65
Log(D) at pH=7.4
1.84
Log(P)
4.34
Log S
-5.26
Log(Vapor Pressure)
-7.96
Melting Point
183.67
pKa Acid
5.03
pKa Basic
7.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8741
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.8070
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7558
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7429
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7417
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7159

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