Cucurbitacin F 25-O-acetate - Compound Card

Cucurbitacin F 25-O-acetate

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Cucurbitacin F 25-O-acetate

Structure
Zoomed Structure
  • Family: Plantae - Cucurbitaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles CC(=O)OC(/C=C/C(=O)[C@@]([C@H]1[C@H](O)C[C@@]2(C1(C)CC(=O)C1(C2CC=C2[C@H]1C[C@H](O)[C@H](C2(C)C)O)C)C)(O)C)(C)C
InChI InChI=1S/C32H48O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25-26,34-35,38-39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22?,25+,26-,29+,30?,31?,32+/m1/s1
InChIKey LMJMTWXDWFWZHV-KLTFEMGSSA-N
Formula C32H48O8
HBA 8
HBD 4
MW 560.73
Rotatable Bonds 5
TPSA 141.36
LogP 3.29
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 560.33
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Cucumis callosus Cucurbitaceae Plantae 217619

Showing of synonyms

  • Add El-Fattah H. (1994). Structure Revision of Cucurbitacin Q1. Phytochemistry, 1994, 36(1), 159-161. [View]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 560.73 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.08
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.87
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.75
Plasma Protein Binding
95.34
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.55
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.39
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.88
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.21
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-1029.19
Rat (Acute)
4.79
Rat (Chronic Oral)
2.34
Fathead Minnow
4.99
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
482.32
Hydration Free Energy
-2.9
Log(D) at pH=7.4
3.39
Log(P)
3.4
Log S
-4.19
Log(Vapor Pressure)
-9.42
Melting Point
207.01
pKa Acid
6.8
pKa Basic
3.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8727
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8008
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7946
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7342
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7214
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7174
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7161
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7111

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