Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2021-09-23 02:50:08 UTC |
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Update Date | 2021-09-23 02:50:08 UTC |
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HMDB ID | HMDB0301826 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | ent-Copalyl diphosphate |
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Description | Ent-copalyl diphosphate, also known as (-)-copalyl diphosphoric acid or 5a,9a,10b-labda-8(20),13-dien-15-yl diphosphate, is a member of the class of compounds known as diterpenoids. Diterpenoids are terpene compounds formed by four isoprene units. Thus, ent-copalyl diphosphate is considered to be an isoprenoid lipid molecule. Ent-copalyl diphosphate is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Ent-copalyl diphosphate can be found in a number of food items such as german camomile, sweet basil, eggplant, and cardoon, which makes ent-copalyl diphosphate a potential biomarker for the consumption of these food products. |
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Structure | C\C(CC[C@@H]1C(=C)CC[C@@H]2C(C)(C)CCC[C@@]12C)=C/COP(O)(=O)OP(O)(O)=O InChI=1S/C20H36O7P2/c1-15(11-14-26-29(24,25)27-28(21,22)23)7-9-17-16(2)8-10-18-19(3,4)12-6-13-20(17,18)5/h11,17-18H,2,6-10,12-14H2,1,3-5H3,(H,24,25)(H2,21,22,23)/b15-11+/t17-,18-,20+/m1/s1 |
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Synonyms | Value | Source |
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(-)-Copalyl diphosphate | ChEBI | 5alpha,9alpha,10beta-Labda-8(20),13-dien-15-yl diphosphate | ChEBI | ent-Copalyl diphosphate | ChEBI | (-)-Copalyl diphosphoric acid | Generator | 5a,9a,10b-Labda-8(20),13-dien-15-yl diphosphate | Generator | 5a,9a,10b-Labda-8(20),13-dien-15-yl diphosphoric acid | Generator | 5alpha,9alpha,10beta-Labda-8(20),13-dien-15-yl diphosphoric acid | Generator | 5Α,9α,10β-labda-8(20),13-dien-15-yl diphosphate | Generator | 5Α,9α,10β-labda-8(20),13-dien-15-yl diphosphoric acid | Generator | ent-Copalyl diphosphoric acid | Generator | 5b,9a,10a-Labda-8(20),13-dien-15-yl diphosphate | Generator | 5b,9a,10a-Labda-8(20),13-dien-15-yl diphosphoric acid | Generator | 5beta,9alpha,10alpha-Labda-8(20),13-dien-15-yl diphosphoric acid | Generator | 5Β,9α,10α-labda-8(20),13-dien-15-yl diphosphate | Generator | 5Β,9α,10α-labda-8(20),13-dien-15-yl diphosphoric acid | Generator |
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Chemical Formula | C20H36O7P2 |
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Average Molecular Weight | 450.4432 |
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Monoisotopic Molecular Weight | 450.19362653 |
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IUPAC Name | [({[(2E)-5-[(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid |
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Traditional Name | (-)-copalyl diphosphate |
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CAS Registry Number | Not Available |
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SMILES | C\C(CC[C@@H]1C(=C)CC[C@@H]2C(C)(C)CCC[C@@]12C)=C/COP(O)(=O)OP(O)(O)=O |
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InChI Identifier | InChI=1S/C20H36O7P2/c1-15(11-14-26-29(24,25)27-28(21,22)23)7-9-17-16(2)8-10-18-19(3,4)12-6-13-20(17,18)5/h11,17-18H,2,6-10,12-14H2,1,3-5H3,(H,24,25)(H2,21,22,23)/b15-11+/t17-,18-,20+/m1/s1 |
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InChI Key | JCAIWDXKLCEQEO-PGHZQYBFSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Diterpenoids |
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Direct Parent | Diterpenoids |
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Alternative Parents | |
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Substituents | - Diterpenoid
- Labdane diterpenoid
- Organic pyrophosphate
- Isoprenoid phosphate
- Monoalkyl phosphate
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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ent-Copalyl diphosphate,1TMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O | 3242.1 | Semi standard non polar | 33892256 | ent-Copalyl diphosphate,1TMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O | 2940.6 | Standard non polar | 33892256 | ent-Copalyl diphosphate,1TMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O | 4099.2 | Standard polar | 33892256 | ent-Copalyl diphosphate,1TMS,isomer #2 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C | 3243.6 | Semi standard non polar | 33892256 | ent-Copalyl diphosphate,1TMS,isomer #2 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C | 2941.1 | Standard non polar | 33892256 | ent-Copalyl diphosphate,1TMS,isomer #2 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C | 4137.0 | Standard polar | 33892256 | ent-Copalyl diphosphate,2TMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C | 3259.1 | Semi standard non polar | 33892256 | ent-Copalyl diphosphate,2TMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C | 3007.7 | Standard non polar | 33892256 | ent-Copalyl diphosphate,2TMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C | 3878.5 | Standard polar | 33892256 | ent-Copalyl diphosphate,2TMS,isomer #2 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3264.0 | Semi standard non polar | 33892256 | ent-Copalyl diphosphate,2TMS,isomer #2 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 2985.7 | Standard non polar | 33892256 | ent-Copalyl diphosphate,2TMS,isomer #2 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3867.8 | Standard polar | 33892256 | ent-Copalyl diphosphate,3TMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3261.6 | Semi standard non polar | 33892256 | ent-Copalyl diphosphate,3TMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3049.4 | Standard non polar | 33892256 | ent-Copalyl diphosphate,3TMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3572.3 | Standard polar | 33892256 | ent-Copalyl diphosphate,1TBDMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O | 3447.6 | Semi standard non polar | 33892256 | ent-Copalyl diphosphate,1TBDMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O | 3134.1 | Standard non polar | 33892256 | ent-Copalyl diphosphate,1TBDMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O | 4236.0 | Standard polar | 33892256 | ent-Copalyl diphosphate,1TBDMS,isomer #2 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C | 3444.3 | Semi standard non polar | 33892256 | ent-Copalyl diphosphate,1TBDMS,isomer #2 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C | 3143.8 | Standard non polar | 33892256 | ent-Copalyl diphosphate,1TBDMS,isomer #2 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C | 4263.5 | Standard polar | 33892256 | ent-Copalyl diphosphate,2TBDMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C | 3654.1 | Semi standard non polar | 33892256 | ent-Copalyl diphosphate,2TBDMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C | 3349.4 | Standard non polar | 33892256 | ent-Copalyl diphosphate,2TBDMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C | 4022.6 | Standard polar | 33892256 | ent-Copalyl diphosphate,2TBDMS,isomer #2 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3652.5 | Semi standard non polar | 33892256 | ent-Copalyl diphosphate,2TBDMS,isomer #2 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3313.2 | Standard non polar | 33892256 | ent-Copalyl diphosphate,2TBDMS,isomer #2 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4037.3 | Standard polar | 33892256 | ent-Copalyl diphosphate,3TBDMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3811.0 | Semi standard non polar | 33892256 | ent-Copalyl diphosphate,3TBDMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3505.0 | Standard non polar | 33892256 | ent-Copalyl diphosphate,3TBDMS,isomer #1 | C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3779.2 | Standard polar | 33892256 |
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