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23,24-dihydrocucurbitacin D
- Family: Plantae - Cucurbitaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | O[C@H]1C[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)CCC(O)(C)C)(O)C)O)C)C(C1=O)(C)C |
|---|---|
| InChI | InChI=1S/C30H46O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,17-20,23,31-32,36-37H,10-15H2,1-8H3/t17-,18+,19-,20+,23+,27+,28-,29+,30+/m1/s1 |
| InChIKey | ITMUUFDDBRYVNJ-VOKXYEOFSA-N |
| Formula | C30H46O7 |
| HBA | 7 |
| HBD | 4 |
| MW | 518.69 |
| Rotatable Bonds | 5 |
| TPSA | 132.13 |
| LogP | 3.15 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 37 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.83 |
| Exact Mass | 518.32 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Bryonia cretica | Cucurbitaceae | Plantae | 61884 |
Showing of synonyms
23,24-dihydrocucurbitacin D
Cucurbitacin R
55903-92-9
Dihydrocucurbitacin D
CHEBI:62218
(2S,4R)-2,16,20,25-tetrahydroxy-9beta,10,14-trimethyl-4,9-cyclo-9,10-seco-16alpha-cholest-5-ene-1,11,22-trione
2b,16a,20,25-Tetrahydroxy-10a-cucurbit-5-ene-3,11,22-trione
2b,16a,20,25-Tetrahydroxy-9b-methyl-19-nor-10a-lanost-5-ene-3,11,22-trione
(2S,8S,9R,10R,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
Tetrahydrocucurbitacin I
2beta,16alpha,20,25-tetrahydroxy-10alpha-cucurbit-5-ene-3,11,22-trione
(10alpha)-2beta,16alpha,20,25-Tetrahydroxy-9beta-methyl-19-norlanosta-5-ene-3,11,22-trione
2beta,16alpha,20,25- tetrahydroxy-9beta-methyl-19-nor-10alpha-lanost-5-ene-3,11,22-trione
CHEMBL564629
SCHEMBL10307357
DTXSID101317423
AKOS040734738
DA-69007
NS00094067
23,24-Dihydrocucurbitacin D (Cucurbitacin R)
Q27131691
- 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:
180535
Cas:
55903-92-9
Zinc:
ZINC000031159436
Chebi:
62218
Nmrshiftdb2:
60065087
Metabolights:
MTBLC62218
Chembl:
CHEMBL564629
CPRiL:
257744
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3CCC(=O)C4
Level: 0
Mol. Weight: 518.69 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.73
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.72
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.72
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.88
- Plasma Protein Binding
- 94.07
- 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
- 6.23
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.78
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.87
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.94
- 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
- -270.15
- Rat (Acute)
- 4.41
- Rat (Chronic Oral)
- 2.1
- Fathead Minnow
- 4.0
- 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
- 494.72
- Hydration Free Energy
- -2.8
- Log(D) at pH=7.4
- 2.74
- Log(P)
- 3.04
- Log S
- -4.2
- Log(Vapor Pressure)
- -9.58
- Melting Point
- 237.65
- pKa Acid
- 5.79
- pKa Basic
- 1.92
| 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 | 0.8588 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8324 |
| Maltose/maltodextrin-binding periplasmic protein | P0AEX9 | MALE_ECOLI | Escherichia coli | 3 | 0.8023 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7300 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7074 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7043 |