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24-methylene cycloart-3-one
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpenoid
| Canonical Smiles | C=C(C(C)C)CCC([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13C2CC[C@@H]2[C@]3(C1)CCC(=O)C2(C)C)C)C |
|---|---|
| InChI | InChI=1S/C31H50O/c1-20(2)21(3)9-10-22(4)23-13-15-29(8)25-12-11-24-27(5,6)26(32)14-16-30(24)19-31(25,30)18-17-28(23,29)7/h20,22-25H,3,9-19H2,1-2,4-8H3/t22?,23-,24+,25?,28-,29+,30-,31+/m1/s1 |
| InChIKey | AEAWOMODYBIREN-CNVWHVCZSA-N |
| Formula | C31H50O |
| HBA | 1 |
| HBD | 0 |
| MW | 438.74 |
| Rotatable Bonds | 5 |
| TPSA | 17.07 |
| LogP | 8.62 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 32 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.9 |
| Exact Mass | 438.39 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Euphorbia helioscopia | Euphorbiaceae | Plantae | 154990 |
Showing of synonyms
24-methylene cycloart-3-one
- Mohamed AH, Hegazy MF, et al. (2012). Euphorbia helioscopia: Chemical constituents and biological activities. International Journal of Phytopharmacology,2012,3(1),78-90. [View]
Pubchem:
162955413
No compound-protein relationship available.
SMILES: C1CC(=O)CC(C1(C234)C2)CCC3C5C(CC4)CCC5
Level: 0
Mol. Weight: 438.74 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.79
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.65
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.75
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 2.37
- Plasma Protein Binding
- 92.35
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- 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
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.18
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.32
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.27
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.66
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -81.11
- Rat (Acute)
- 2.22
- Rat (Chronic Oral)
- 1.75
- Fathead Minnow
- 4.21
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 428.58
- Hydration Free Energy
- -2.83
- Log(D) at pH=7.4
- 7.27
- Log(P)
- 8.58
- Log S
- -6.74
- Log(Vapor Pressure)
- -7.76
- Melting Point
- 164.17
- pKa Acid
- 11.97
- pKa Basic
- 7.3
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.9330 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.9330 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.9169 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.9169 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9083 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9083 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8995 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8995 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8942 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8942 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8927 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8927 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8856 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8856 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8798 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8798 |
| Beta-elicitin cryptogein | P15570 | ELIB_PHYCR | Phytophthora cryptogea | 4 | 0.8749 |
| Beta-elicitin cryptogein | P15570 | ELIB_PHYCR | Phytophthora cryptogea | 4 | 0.8749 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8646 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8646 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8604 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8604 |
| Retinol-binding protein 2 | P50120 | RET2_HUMAN | Homo sapiens | 3 | 0.8589 |
| Retinol-binding protein 2 | P50120 | RET2_HUMAN | Homo sapiens | 3 | 0.8589 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8490 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8490 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8445 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8445 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8289 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8289 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.8247 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.8247 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8201 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8201 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 3 | 0.8198 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 3 | 0.8198 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.8121 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.8121 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.8096 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.8096 |
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.8059 |
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.8059 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.8026 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.8026 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.8024 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.8024 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7954 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7954 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7904 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7904 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7870 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7870 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7812 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7812 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7651 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7651 |
| Retinol-binding protein 2 | P50120 | RET2_HUMAN | Homo sapiens | 3 | 0.7619 |
| Retinol-binding protein 2 | P50120 | RET2_HUMAN | Homo sapiens | 3 | 0.7619 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7594 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7594 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7585 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7585 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7570 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7570 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7557 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7557 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7556 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7556 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7523 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7523 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7463 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7463 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7431 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7431 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7415 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7415 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 2 | 0.7400 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 2 | 0.7400 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.7389 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.7389 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 2 | 0.7373 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 2 | 0.7373 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7371 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7371 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7350 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7350 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7303 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7303 |
| Vitamin D3 receptor | P13053 | VDR_RAT | Rattus norvegicus | 3 | 0.7290 |
| Vitamin D3 receptor | P13053 | VDR_RAT | Rattus norvegicus | 3 | 0.7290 |
| Lanosterol synthase | P48449 | ERG7_HUMAN | Homo sapiens | 3 | 0.7287 |
| Lanosterol synthase | P48449 | ERG7_HUMAN | Homo sapiens | 3 | 0.7287 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 2 | 0.7282 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 2 | 0.7282 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7263 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7263 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7252 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7252 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7238 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7238 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7196 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7196 |
| Vitamin D3 receptor | P13053 | VDR_RAT | Rattus norvegicus | 3 | 0.7192 |
| Vitamin D3 receptor | P13053 | VDR_RAT | Rattus norvegicus | 3 | 0.7192 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7150 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7150 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7144 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7144 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7103 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7103 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7099 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7099 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P00189 | CP11A_BOVIN | Bos taurus | 3 | 0.7088 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P00189 | CP11A_BOVIN | Bos taurus | 3 | 0.7088 |
| Retinol-binding protein 1 | P09455 | RET1_HUMAN | Homo sapiens | 3 | 0.7068 |
| Retinol-binding protein 1 | P09455 | RET1_HUMAN | Homo sapiens | 3 | 0.7068 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7058 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7058 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7053 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7053 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7052 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7052 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7036 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7036 |