Cucurbitacin J - Compound Card

Cucurbitacin J

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Cucurbitacin J

Structure
Zoomed Structure
  • Family: Plantae - Cucurbitaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles OC1=C[C@@H]2C(=CC[C@@H]3[C@@]2(C)C(=O)C[C@]2([C@@]3(C)C[C@H]([C@@H]2[C@](C(=O)CC(C(O)(C)C)O)(O)C)O)C)C(C1=O)(C)C
InChI InChI=1S/C30H44O8/c1-25(2)15-9-10-19-27(5)13-18(32)23(30(8,38)21(34)12-20(33)26(3,4)37)28(27,6)14-22(35)29(19,7)16(15)11-17(31)24(25)36/h9,11,16,18-20,23,31-33,37-38H,10,12-14H2,1-8H3/t16-,18-,19+,20?,23+,27+,28-,29+,30+/m1/s1
InChIKey FBGLZDYMEULGSX-IDZQOQCMSA-N
Formula C30H44O8
HBA 8
HBD 5
MW 532.67
Rotatable Bonds 5
TPSA 152.36
LogP 2.81
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.77
Exact Mass 532.3
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Bryonia cretica Cucurbitaceae Plantae 61884

Showing of synonyms

  • Matsuda H, Nakashima S, et al. (2010). Cucurbitane-Type Triterpenes with Anti-proliferative Effects on U937 Cells from an Egyptian Natural Medicine, Bryonia cretica: Structures of New Triterpene Glycosides, Bryoniaosides A and B. Chemical & pharmaceutical bulletin, 2010, 58(5), 747-51. [View] [PubMed]
Pubchem: 441819
Kegg Ligand: C08801
Nmrshiftdb2: 80005229

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3C=CC(=O)C4

Level: 0

Mol. Weight: 532.67 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.01
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.88
Plasma Protein Binding
102.2
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
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
3.48
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.25
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.95
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.75
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-406.35
Rat (Acute)
4.53
Rat (Chronic Oral)
2.61
Fathead Minnow
4.07
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
518.99
Hydration Free Energy
-2.81
Log(D) at pH=7.4
2.74
Log(P)
2.33
Log S
-3.57
Log(Vapor Pressure)
-9.9
Melting Point
245.98
pKa Acid
5.15
pKa Basic
3.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8429
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.8009
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7866
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7547
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7228
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7167
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7030

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