Methy1-(3E,7Z,11E)-20-oxo-cembra-3,7,1l,15-tetraen-19-oate - Compound Card

Methy1-(3E,7Z,11E)-20-oxo-cembra-3,7,1l,15-tetraen-19-oate

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Methy1-(3E,7Z,11E)-20-oxo-cembra-3,7,1l,15-tetraen-19-oate

Structure
Zoomed Structure
  • Family: Plantae - Capparaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dammarane Type Triterpene
Canonical Smiles COC(=O)/C/1=C\CC/C(=C/CC(CC/C(=C\CC1)/C=O)C(=C)C)/C
InChI InChI=1S/C21H30O3/c1-16(2)19-13-11-17(3)7-5-9-20(21(23)24-4)10-6-8-18(15-22)12-14-19/h8-9,11,15,19H,1,5-7,10,12-14H2,2-4H3/b17-11+,18-8+,20-9-
InChIKey WAOIDNZOTULWQY-YIWRKYCBSA-N
Formula C21H30O3
HBA 3
HBD 0
MW 330.47
Rotatable Bonds 3
TPSA 43.37
LogP 5.09
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 330.22
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Cleome africana Capparaceae Plantae 860685

Showing of synonyms

  • Nagaya H, Tobita Y, et al. (1997). Cytotoxic triterpenes from Cleome africana. Phytochemistry, 1997, 44(6), 1115-9. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1=CCCC=CCCCCC=CCC1

Level: 0

Mol. Weight: 330.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.280
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.670
Plasma Protein Binding
52.95
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
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
2.840
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.060
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.780
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.020
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
3.430
Rat (Acute)
2.290
Rat (Chronic Oral)
1.850
Fathead Minnow
5.110
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
376.550
Hydration Free Energy
-5.670
Log(D) at pH=7.4
4.180
Log(P)
6.36
Log S
-4.31
Log(Vapor Pressure)
-5.41
Melting Point
38.6
pKa Acid
8.48
pKa Basic
5.59
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9791
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9767
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9655
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9368
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9152
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9142
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.9060
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8959
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8896
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8876
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8866
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8859
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8692
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8639
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8565
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8537
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8475
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8403
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8380
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8343
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8335
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8124
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8065
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8046
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8040
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8005
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.8004
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7999
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7942
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7935
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7926
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7905
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7873
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7868
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7849
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7821
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7808
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7794
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7789
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7783
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7775
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7767
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7737
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7734
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 2 0.7722
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7706
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7689
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7662
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7655
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7650
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7628
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7623
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7605
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7578
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7575
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7572
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7570
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7562
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7557
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7549
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7541
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7536
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7522
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7508
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7484
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7470
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7467
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7454
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7437
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7421
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7405
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7401
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7394
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7387
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7384
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7377
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7374
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7353
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7350
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7350
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7350
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7346
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 2 0.7324
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7293
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 2 0.7287
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7270
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7258
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7254
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7253
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7252
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7243
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7238
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7229
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7228
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7227
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7214
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7200
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7189
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7180
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7179
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7171
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7168
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7158
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7154
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7153
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7152
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7147
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7146
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7124
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7115
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 2 0.7114
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7114
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7109
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 2 0.7096
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 2 0.7084
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7072
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7069
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7061
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7050
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7044
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7039
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7022
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7015
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7002

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