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Uzarigenin
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Steroid
- Subclass: Steroid Lactone
| Canonical Smiles | O[C@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)C |
|---|---|
| InChI | InChI=1S/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16-,17+,18-,19+,21-,22+,23-/m0/s1 |
| InChIKey | XZTUSOXSLKTKJQ-CIXPXFMPSA-N |
| Formula | C23H34O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 374.52 |
| Rotatable Bonds | 1 |
| TPSA | 66.76 |
| LogP | 3.6 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.87 |
| Exact Mass | 374.25 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Gomphocarpus sinaicus | Apocynaceae | Plantae | 2291033 |
| 2 | Calotropis procera | Apocynaceae | Plantae | 141467 |
| 3 | Gomphocarpus fruticosus | Apocynaceae | Plantae | 219240 |
Showing of synonyms
Uzarigenin
466-09-1
ODORIGENIN B
Urarigenin
Odorigeni
K9ZR7LI283
(3.beta.,5.alpha.)-3,14-Dihydroxycard-20(22)-enolide
Card-20(22)-enolide, 3,14-dihydroxy-, (3.beta.,5.alpha.)-
4-18-00-01470 (Beilstein Handbook Reference)
EINECS 207-373-0
NSC 119993
BRN 0095446
UNII-K9ZR7LI283
3-beta-14-beta-5-Allo-cardenolid [German]
NSC-119993
NSC-277290
3beta,14-Dihydroxy-5alpha-card-20(22)-enolide
3-beta-14-beta-5-Allo-cardenolid
3-beta,14-Dihydroxy-5-alpha-card-20(22)-enolide
ODORIGENIN
Uzarigenin (Odorigenin)
UZARIGENIN [MI]
NSC 277290
5alpha-Card-20(22)-enolide, 3beta,14-dihydroxy-
5-alpha-Card-20(22)-enolide, 3-beta,14-dihydroxy-
CHEMBL109863
SCHEMBL1152953
XZTUSOXSLKTKJQ-CIXPXFMPSA-N
Card-20(22)-enolide, 3,14-dihydroxy-, (3beta,5alpha)-
DTXSID901017013
HY-N1107
AKOS040762476
FS-9903
FU42614
NCGC00384854-01
3,14-Dihydroxycard-20(22)-enolide #
3-.beta.-14-.beta.-5-Allo-cardenolid
CS-0016395
NS00080556
Q27282143
5.alpha.-Card-20(22)-enolide, 3.beta.,14-dihydroxy-
NCGC00384854-01_C23H34O4_Card-20(22)-enolide, 3,14-dihydroxy-, (3beta,5alpha)-
- Marzouk A.M, Osman S.M, et al. (2016). A new pregnane glycoside from Gomphocarpus fruticosus growing in Egypt. Natural product research, 2016, 30(9), 1060-7. [View] [PubMed]
- El-Askary H, Holzl J, et al. (1993). Cardenolide glycosides with doubly linked sugars from Gomphocarpus sinaicus. Phytochemistry,1993,34(5),1399-1402. [View]
- Shaker KM, Morsy N, et al. (2010). Secondary metabolites from Calotropis procera (Aiton). Phytochemistry Letters,2010,3(4),212-216. [View]
Pubchem:
92760
Cas:
466-09-1
Gnps:
CCMSLIB00006581616
Zinc:
ZINC000004073972
Nmrshiftdb2:
60070143
Chembl:
CHEMBL109863
CPRiL:
21526
SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)CCCC5
Level: 1
Mol. Weight: 374.52 g/mol
SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4
Level: 0
Mol. Weight: 374.52 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 374.52 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.67
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.8
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.45
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.91
- Plasma Protein Binding
- 62.14
- 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
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.11
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.22
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.43
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.79
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Toxic
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -13.82
- Rat (Acute)
- 2.46
- Rat (Chronic Oral)
- 1.51
- Fathead Minnow
- 3.9
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 460.58
- Hydration Free Energy
- -4.13
- Log(D) at pH=7.4
- 2.8
- Log(P)
- 2.86
- Log S
- -4.54
- Log(Vapor Pressure)
- -8.36
- Melting Point
- 236.34
- pKa Acid
- 9.76
- pKa Basic
- 7.98
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9245 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9245 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8876 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8876 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.8732 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.8732 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8683 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8683 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8414 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8414 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 4 | 0.8230 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 4 | 0.8230 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8192 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8192 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8134 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8134 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8125 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8125 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.8106 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.8106 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7848 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7848 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7384 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7384 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7230 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7230 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7216 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7216 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7094 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7094 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7009 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7009 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7004 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7004 |