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23,24-dihydrocucurbitacin B
- 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(=O)C2(C)C)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/h10,19-22,25,34-35,39H,11-16H2,1-9H3/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1 |
| InChIKey | QZJJDOYZVRUEDY-NRNCYQGDSA-N |
| Formula | C32H48O8 |
| HBA | 8 |
| HBD | 3 |
| MW | 560.73 |
| Rotatable Bonds | 6 |
| TPSA | 138.2 |
| LogP | 3.72 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.81 |
| Exact Mass | 560.33 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Bryonia cretica | Cucurbitaceae | Plantae | 61884 |
Showing of synonyms
23,24-dihydrocucurbitacin B
DIHYDROCUCURBITACIN B
13201-14-4
CHEBI:62217
NSC-106401
(2S,4R)-2,16beta,20-trihydroxy-9beta,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholest-5-en-25-yl acetate
(2.BETA.,9.BETA.,10.ALPHA.,16.ALPHA.)-25-(ACETYLOXY)-2,16,20-TRIHYDROXY-9-METHYL-19-NORLANOST-5-ENE-3,11,22-TRIONE
19-NORLANOST-5-ENE-3,11,22-TRIONE, 25-(ACETYLOXY)-2,16,20-TRIHYDROXY-9-METHYL-, (2.BETA.,9.BETA.,10.ALPHA.,16.ALPHA.)-
Cucurbitacin B, 23,24-dihydro-
25-Acetoxy-2b,16a,20-trihydroxy-10a-cucurbit-5-ene-3,11,22-trione
25-Acetoxy-2I2,16I+-,20-trihydroxy-10I+--cucurbit-5-ene-3,11,22-trione
(2BETA,9BETA,10ALPHA,16ALPHA)-25-(ACETYLOXY)-2,16,20-TRIHYDROXY-9-METHYL-19-NORLANOST-5-ENE-3,11,22-TRIONE
19-NORLANOST-5-ENE-3,11,22-TRIONE, 25-(ACETYLOXY)-2,16,20-TRIHYDROXY-9-METHYL-, (2BETA,9BETA,10ALPHA,16ALPHA)-
2b,16a,20,25-Tetrahydroxy-9-methyl-19-nor-9b,10a-lanost-5-ene-3,11,22-trione, 25-acetate
2b,16a,20,25-Tetrahydroxy-9-methyl-19-nor-9b,10a-lanost-5-ene-3,11,22-trione, 25-acetic acid
2b,16a,20,25-Tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9b,10a-lanost-5-en-25-yl acetate
2b,16a,20,25-Tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9b,10a-lanost-5-en-25-yl acetic acid
2beta,16alpha,20,25-Tetrahydroxy-9-methyl-19-nor-9beta,10alpha-lanost-5-ene-3,11,22-trione, 25-acetic acid
2beta,16alpha,20,25-Tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9beta,10alpha-lanost-5-en-25-yl acetic acid
Qzjjdoyzvruedy-uhfffaoysa-n
Cucurbitacin B, dihydro-
(10alpha)-25-(Acetyloxy)-2beta,16alpha,20-trihydroxy-9beta-methyl-19-norlanost-5-ene-3,11,22-trione
[(6R)-6-[(2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxoheptan-2-yl] acetate
25-acetoxy-2beta,16alpha,20-trihydroxy-10alpha-cucurbit-5-ene-3,11,22-trione
2beta,16alpha,20,25-tetrahydroxy-9-methyl-19-nor-9beta,10alpha-lanost-5-ene-3,11,22-trione, 25-acetate
2beta,16alpha,20,25-tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9beta,10alpha-lanost-5-en-25-yl acetate
CHEMBL553851
DTXSID701314710
HY-N4171
NAA20114
NSC106401
AKOS037514506
DA-62878
MS-30184
CS-0032304
NS00094065
C20787
G14140
Q27131690
(10|A)-25-(Acetyloxy)-2|A,16|A,20-trihydroxy-9|A-methyl-19-norlanost-5-ene-3,11,22-trione
- 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:
267250
Cas:
13201-14-4
Zinc:
ZINC000004962910
Chebi:
62217
Nmrshiftdb2:
60024640
Metabolights:
MTBLC62217
Chembl:
CHEMBL553851
CPRiL:
100006
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3CCC(=O)C4
Level: 0
Mol. Weight: 560.73 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.76
- 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
- -1.31
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.83
- Plasma Protein Binding
- 101.17
- 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
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.25
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.54
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.01
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.59
- 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
- -1030.28
- Rat (Acute)
- 4.32
- Rat (Chronic Oral)
- 2.04
- Fathead Minnow
- 4.17
- 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
- 482.97
- Hydration Free Energy
- -2.83
- Log(D) at pH=7.4
- 3.52
- Log(P)
- 3.49
- Log S
- -4.8
- Log(Vapor Pressure)
- -9.22
- Melting Point
- 214.37
- pKa Acid
- 6.12
- pKa Basic
- 1.48
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.9132 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8947 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7958 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7917 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7530 |
| Lactaldehyde dehydrogenase | P25553 | ALDA_ECOLI | Escherichia coli | 3 | 0.7447 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7432 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7376 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7359 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7265 |
| Angiotensin-converting enzyme | Q10714 | ACE_DROME | Drosophila melanogaster | 3 | 0.7211 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7152 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7126 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7106 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7104 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7103 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7051 |
| TamL | D3Y1I2 | D3Y1I2_9ACTN | Streptomyces sp. 307-9 | 2 | 0.7005 |