Select a section from the left sidebar
Copalic acid
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Diterpene
| Canonical Smiles | C/C(=C\C(=O)O)/CC[C@@H]1C(=C)CC[C@H]2[C@@]1(C)CCCC2(C)C |
|---|---|
| InChI | InChI=1S/C20H32O2/c1-14(13-18(21)22)7-9-16-15(2)8-10-17-19(3,4)11-6-12-20(16,17)5/h13,16-17H,2,6-12H2,1,3-5H3,(H,21,22)/b14-13+/t16-,17-,20+/m1/s1 |
| InChIKey | JFQBNOIJWROZGE-HPMXROJMSA-N |
| Formula | C20H32O2 |
| HBA | 1 |
| HBD | 1 |
| MW | 304.47 |
| Rotatable Bonds | 4 |
| TPSA | 37.3 |
| LogP | 5.6 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.75 |
| Exact Mass | 304.24 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Senna alata | Leguminosae/Fabaceae | Plantae | 53923 |
Showing of synonyms
Copalic acid
(E)-5-[(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid
Copalate
(E)-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl)-3-methylpent-2-enoic acid
Inchi=1/c20h32o2/c1-14(13-18(21)22)7-9-16-15(2)8-10-17-19(3,4)11-6-12-20(16,17)5/h13,16-17h,2,6-12h2,1,3-5h3,(h,21,22)/b14-13+/t16-,17-,20+/m1/s
Jfqbnoijwrozge-tzrhrlilsa-n
Jfqbnoijwrozge-vbracaiisa-n
Ent-Copalic acid
(+/-)-Copalic acid
Copalic acid, (-)-
6LTQ2LP2NB
Copalic acid, (+/-)-
CHEMBL102201
Q8T4C64T5F
CHEBI:170112
DTXSID701316809
(2E)-5-[(1R,4aR,8aR)-Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]-3-methyl-2-pentenoic acid
(E)-5-[(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decalin-1-yl]-3-methyl-pent-2-enoic acid
2-Pentenoic acid, 5-(decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl)-3-methyl-, [1alpha(E),4abeta,8aalpha]-(+/-)-
2-Pentenoic acid, 5-(decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl)-3-methyl-, [1R-[1alpha(E),4abeta,8aalpha]]-
2-Pentenoic acid, 5-[(1R,4aR,8aR)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]-3-methyl-, (2E)-
2-Pentenoic acid, 5-[(1R,4aR,8aR)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]-3-methyl-, (2E)-rel-
80657-12-1
Rel-(2E)-5-[(1R,4aR,8aR)-Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]-3-methyl-2-pentenoic acid
- Fotso SC, Tadjong AT, et al. (2021). Chemical constituents and antimicrobial activities of some isolated compounds from the Cameroonian species of Senna alata ( Cassia alata L. Roxb synonym, The plant list 2013). (Leguminosae). Town Planning Review, 2021, 5, 37-43. [View]
Pubchem:
11162521
Cas:
80657-12-1
Zinc:
ZINC000026742566
Chebi:
170112
Nmrshiftdb2:
20107456
Chembl:
CHEMBL102201
CPRiL:
152650
SMILES: C=C(C1)CCC(C12)CCCC2
Level: 0
Mol. Weight: 304.47 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.55
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.65
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.6
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.25
- Plasma Protein Binding
- 87.27
- 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
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- -0.26
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.88
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.09
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.15
- 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
- 0.73
- Rat (Acute)
- 2.21
- Rat (Chronic Oral)
- 1.74
- Fathead Minnow
- 3.95
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 357.16
- Hydration Free Energy
- -3.98
- Log(D) at pH=7.4
- 2.61
- Log(P)
- 5.89
- Log S
- -4.97
- Log(Vapor Pressure)
- -6.5
- Melting Point
- 137.6
- pKa Acid
- 6.51
- pKa Basic
- 7.48
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Deacetoxycephalosporin C synthase | P18548 | CEFE_STRCL | Streptomyces clavuligerus | 3 | 0.9387 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 3 | 0.8772 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8600 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8523 |
| Branched-chain-amino-acid aminotransferase, mitochondrial | O15382 | BCAT2_HUMAN | Homo sapiens | 3 | 0.8471 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8455 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8370 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.8364 |
| Retinol-binding protein 2 | P50120 | RET2_HUMAN | Homo sapiens | 3 | 0.8280 |
| 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase | P9WNH5 | HSAD_MYCTU | Mycobacterium tuberculosis | 3 | 0.8273 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8109 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.8074 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.8043 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8037 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.8017 |
| Vitamin D3 receptor | P13053 | VDR_RAT | Rattus norvegicus | 4 | 0.7998 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7985 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7945 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7834 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7759 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7645 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 2 | 0.7617 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7555 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7488 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7476 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7472 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7443 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7443 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7442 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7431 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7430 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7423 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7415 |
| Retinol-binding protein 1 | P09455 | RET1_HUMAN | Homo sapiens | 3 | 0.7398 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7376 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7372 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7351 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7348 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7343 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 2 | 0.7336 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7331 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7325 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7314 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7303 |
| Retinaldehyde-binding protein 1 | P12271 | RLBP1_HUMAN | Homo sapiens | 4 | 0.7301 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7298 |
| Putative cytochrome P450 120 | Q59990 | CP120_SYNY3 | Synechocystis sp | 3 | 0.7295 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7251 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7238 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7198 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7188 |
| Cellular retinol-binding protein type II | Q8UVG6 | Q8UVG6_DANRE | Danio rerio | 3 | 0.7182 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 2 | 0.7170 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7165 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7160 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 2 | 0.7157 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7151 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7140 |
| Cellular retinoic acid-binding protein 2 | P29373 | RABP2_HUMAN | Homo sapiens | 3 | 0.7118 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7115 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7111 |
| Lanosterol synthase | P48449 | ERG7_HUMAN | Homo sapiens | 3 | 0.7111 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7090 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7072 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7072 |
| Multidrug transporter MdfA | P0AEY8 | MDFA_ECOLI | Escherichia coli | 3 | 0.7063 |
| Pyrrolysine--tRNA ligase | Q8PWY1 | PYLS_METMA | Methanosarcina mazei | 2 | 0.7049 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 3 | 0.7047 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 2 | 0.7047 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 2 | 0.7045 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7019 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7008 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7004 |