3-oxo-24-methylenecycloartane - Compound Card

3-oxo-24-methylenecycloartane

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3-oxo-24-methylenecycloartane

Structure
Zoomed Structure
  • Family: Plantae - Arecaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles C=C(C(C)C)CCC([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13C2CCC2[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-KXDMVREESA-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 Sabal peregrina Arecaceae Plantae 151838

Showing of synonyms

  • El-Dib R, Kaloga M, et al. (2004). Sablacaurin A and B, two 19-nor-3,4-seco-lanostane-type triterpenoids from Sabal causiarum and Sabal blackburniana, respectively. Phytochemistry,2004,65(8),1153-1157. [View] [PubMed]
Pubchem: 3083719

No compound-protein relationship available.

Structure

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
-2.76

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.37
Plasma Protein Binding
91.56
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
7.12
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.43
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
6.68
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
-80.43
Rat (Acute)
2.2
Rat (Chronic Oral)
1.75
Fathead Minnow
4.31
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
427.48
Hydration Free Energy
-2.83
Log(D) at pH=7.4
7.2
Log(P)
8.56
Log S
-6.74
Log(Vapor Pressure)
-7.65
Melting Point
161.46
pKa Acid
11.97
pKa Basic
7.33
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9564
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9564
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9444
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9444
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9381
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9381
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9381
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9381
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9251
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9251
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9032
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9032
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.9016
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.9016
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8897
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8897
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8755
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8755
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8635
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8635
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8581
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8581
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8515
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8515
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.8422
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.8422
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8391
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8391
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8318
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8318
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8221
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8221
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8160
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8160
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8097
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8097
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8088
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8088
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8055
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8055
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8050
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8050
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8030
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8030
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8027
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8027
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7988
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7988
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7963
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7963
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7955
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7955
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7947
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7947
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7907
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7907
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7876
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7876
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7857
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7857
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7802
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7802
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7780
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7780
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7776
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7776
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7775
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7775
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7737
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7737
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7707
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7707
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7603
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7603
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7602
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7602
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7585
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7585
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7574
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7574
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7533
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7533
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7515
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7515
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7514
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7514
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7494
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7494
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7473
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7473
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7406
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7406
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7389
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7389
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7379
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7379
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7317
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7317
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7284
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7284
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7266
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7266
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7264
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7264
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7261
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7261
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7254
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7254
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7243
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7243
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7236
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7236
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7202
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7202
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7177
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7177
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7137
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7137
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7135
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7135
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7127
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7127
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7126
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7126
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7113
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7113
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7095
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7095
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7093
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7093
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7070
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7070
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7061
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7061
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7059
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7059
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7052
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7052
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7043
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7043
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7043
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7043
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7036
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7036
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7014
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7014
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7012
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7012
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7006
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7006
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7001
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7001

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