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Cucurbitacin B
- 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([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/C32H46O8/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/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1 |
| InChIKey | IXQKXEUSCPEQRD-DKRGWESNSA-N |
| Formula | C32H46O8 |
| HBA | 8 |
| HBD | 3 |
| MW | 558.71 |
| Rotatable Bonds | 5 |
| TPSA | 138.2 |
| LogP | 3.5 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.75 |
| Exact Mass | 558.32 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Bryonia cretica | Cucurbitaceae | Plantae | 61884 |
Showing of synonyms
Cucurbitacin B
Amarine
Datisca principle B
DATISCACIN
Datiscn Principle B
(+)-Cucurbitacin B
Cucurbitacine B
1,2-Dihydro-alpha-elaterin
CHEBI:3941
UNII-0115W5MABF
0115W5MABF
HSDB 3476
NSC 49451
NSC-49451
NSC 144154
NSC-144154
CUCURBITACIN B [MI]
[(E,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-oxohept-3-en-2-yl] acetate
1,2-DIHYDRO-.ALPHA.-ELATERIN
25-(Acetyloxy)-2,16,20-trihydroxy-9-methyl-19-norlanosta-5,23-diene-3,11,22-trione
19-Nor-9beta,10alpha-lanosta-5,23-diene-3,11,22-trione, 2beta,16alpha,20,25-tetrahydroxy-9-methyl-, 25-acetate
19-Norlanosta-5,23-diene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (2.beta.,9.beta.,10.alpha.,16.alpha.,23E)-
19-Norlanosta-5,23-diene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (2beta,9beta,10alpha,16alpha,23E)-
(2.BETA.,9.BETA.,10.ALPHA.,16.ALPHA.,23E)-25-(ACETYLOXY)-2,16,20-TRIHYDROXY-9-METHYL-19-NORLANOSTA-5,23-DIENE-3,11,22-TRIONE
(2beta,9beta,10alpha,16alpha,23E)-25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-19-Norlanosta-5,23-diene-3,11,22-trione
(2S,4R,23E)-2,16beta,20-trihydroxy-9beta,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-5,23-dien-25-yl acetate
19-Nor-9-beta,10-alpha-lanosta-5,23-diene-3,11,22-trione, 2-beta,16-alpha,20,25-tetrahydroxy-9-methyl-, 25-acetate
2beta,16alpha,20,25-tetrahydroxy-9-methyl-19-nor-9beta,10alpha-lanosta-5,23-diene-3,11,22-trione, 25-acetate
2beta,16alpha,20,25-tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9beta,10alpha-lanosta-5,23-dien-25-yl acetate
((E,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-Oxohept-3-En-2-Yl) Acetate
1,2Dihydroalphaelaterin
1,2-Dihydro-a-elaterin
1,2-Dihydro-I+--elaterin
CUCURBITACIN B [INCI]
CUCURBITACIN R DATISCA PRINCIPLE B
CUCURBITACIN R-DATISCA PRINCIPLE B
25(Acetyloxy)2,16,20trihydroxy9methyl19norlanosta5,23diene3,11,22trione
19-Norlanosta-5,23-diene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (2beta,9beta,10alpha,16alpha,23E)-(9CI)
19Nor9beta,10alphalanosta5,23diene3,11,22trione, 2beta,16alpha,20,25tetrahydroxy9methyl, 25acetate
19Norlanosta5,23diene3,11,22trione, 25(acetyloxy)2,16,20trihydroxy9methyl, (2beta,9beta,10alpha,16alpha,23E)
2b,16a,20,25-Tetrahydroxy-9-methyl-19-nor-9b,10a-lanosta-5,23-diene-3,11,22-trione, 25-acetate
2b,16a,20,25-Tetrahydroxy-9-methyl-19-nor-9b,10a-lanosta-5,23-diene-3,11,22-trione, 25-acetic acid
2b,16a,20,25-Tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9b,10a-lanosta-5,23-dien-25-yl acetate
2b,16a,20,25-Tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9b,10a-lanosta-5,23-dien-25-yl acetic acid
2beta,16alpha,20,25-Tetrahydroxy-9-methyl-19-nor-9beta,10alpha-lanosta-5,23-diene-3,11,22-trione, 25-acetic acid
2beta,16alpha,20,25-Tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9beta,10alpha-lanosta-5,23-dien-25-yl acetic acid
683-121-7
6199-67-3
CHEMBL508185
CUCURBITACIN R - DATISCA PRINCIPLE B
NSC49451
Cucurbitacin B hydrate
(R,E)-6-((2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate
Cucurbitacine (B)
Cucurbitacin-B
MLS002702988
Cucurbitacin B?
19-nor-9.beta.,23-diene-3,11,22-trione, 9-methyl-2.beta.,16.alpha.,20,25-tetrahydroxy-, 25-acetate
19-Norlanosta-5,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (2.beta.,9.beta.,10.alpha.,16.alpha.,23E)-
MFCD07778083
CUCURBITACINB
Cucurbitacin B (Standard)
SCHEMBL231815
GTPL12432
HY-N0416R
DTXSID501316196
HY-N0416
BDBM50628744
LMST01010104
NSC144154
S8165
AKOS015897085
CCG-270043
CS-3816
FC66008
AC-34283
Cucurbitacin B hydrate, >=97% (HPLC)
DA-72423
C3442
NS00094064
C08794
Q27106259
(3E,6R)-6-[(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0?,?.0??,??]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate
19-Norlanosta-5,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, [2.beta.,.gamma.,.beta.,10.alpha.,16.alpha.]-
- 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:
5281316
Cas:
6199-67-3
Gnps:
CCMSLIB00006494560
Zinc:
ZINC000004097797
Kegg Ligand:
C08794
Chebi:
3941
Nmrshiftdb2:
60024631
Metabolights:
MTBLC3941
Chembl:
CHEMBL508185
CPRiL:
60385
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3CCC(=O)C4
Level: 0
Mol. Weight: 558.71 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.81
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.71
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.39
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.82
- Plasma Protein Binding
- 99.72
- 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
- 6.43
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.34
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.05
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.83
- 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
- -1029.55
- Rat (Acute)
- 4.4
- Rat (Chronic Oral)
- 2.15
- Fathead Minnow
- 4.55
- 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
- 479.35
- Hydration Free Energy
- -2.86
- Log(D) at pH=7.4
- 3.32
- Log(P)
- 3.27
- Log S
- -4.81
- Log(Vapor Pressure)
- -9.28
- Melting Point
- 222.84
- pKa Acid
- 6.66
- pKa Basic
- 1.99
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7850 |
| TamL | D3Y1I2 | D3Y1I2_9ACTN | Streptomyces sp. 307-9 | 3 | 0.7716 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7503 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7433 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7378 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7075 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7022 |