23,24-dihydrocucurbitacin F 25-O-acetate - Compound Card

23,24-dihydrocucurbitacin F 25-O-acetate

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23,24-dihydrocucurbitacin F 25-O-acetate

Structure
Zoomed Structure
  • Family: Plantae - Cucurbitaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles CC(=O)OC(CCC(=O)[C@@]([C@H]1[C@H](O)C[C@@]2([C@]1(C)CC(=O)[C@@]1([C@H]2CC=C2[C@H]1C[C@H](O)[C@H](C2(C)C)O)C)C)(O)C)(C)C
InChI InChI=1S/C32H50O8/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/h10,19-22,25-26,34-35,38-39H,11-16H2,1-9H3/t19-,20+,21-,22+,25+,26-,29+,30-,31+,32+/m1/s1
InChIKey LKYNAQSYQLFTCM-GYXNDICUSA-N
Formula C32H50O8
HBA 8
HBD 4
MW 562.74
Rotatable Bonds 6
TPSA 141.36
LogP 3.52
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.84
Exact Mass 562.35
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]
Pubchem: 181183
Nmrshiftdb2: 70103824
CPRiL: 80998
Structure

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

Level: 0

Mol. Weight: 562.74 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.99
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.84
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.76
Plasma Protein Binding
98.18
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
4.66
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.95
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.84
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.01
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
Safe
T. Pyriformis
-1029.88
Rat (Acute)
4.84
Rat (Chronic Oral)
2.22
Fathead Minnow
3.61
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
486.78
Hydration Free Energy
-2.87
Log(D) at pH=7.4
3.59
Log(P)
3.54
Log S
-4.25
Log(Vapor Pressure)
-9.68
Melting Point
204.42
pKa Acid
6.35
pKa Basic
3.22
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8557
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8487
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7960
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7570
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7525
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7494
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7378
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7329
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7103
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7031

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