[
  {
    "id": "lactic-acid",
    "name": "L-Lactic acid",
    "role_label": "monomer",
    "role": "Fermentation product and parent hydroxy acid of PLA; the (S)-enantiomer.",
    "smiles": "C[C@H](O)C(=O)O",
    "cid": 107689,
    "inchikey": "JVTAAEKCZFNVCJ-REOHCLBHSA-N",
    "routes": [
      "pla"
    ],
    "ref": "auras2004"
  },
  {
    "id": "l-lactide",
    "name": "L-Lactide",
    "role_label": "monomer",
    "role": "Cyclic dimer of L-lactic acid; ring-opening polymerisation of lactide gives high-molar-mass PLA.",
    "smiles": "C[C@H]1C(=O)O[C@H](C(=O)O1)C",
    "cid": 107983,
    "inchikey": "JJTUDXZGHPGLLC-IMJSIDKUSA-N",
    "routes": [
      "pla"
    ],
    "ref": "dechycabaret2004"
  },
  {
    "id": "pla-ru",
    "name": "Poly(L-lactide)",
    "role_label": "repeat unit",
    "role": "Repeat unit of PLLA. Hydrolysis returns L-lactic acid, which fixes the stereocentre as (S).",
    "smiles": "*O[C@@H](C)C(*)=O",
    "hydrolysis": [
      "lactic-acid"
    ],
    "routes": [
      "pla"
    ],
    "ref": "tsuji2005"
  },
  {
    "id": "sn-oct2",
    "name": "Tin(II) 2-ethylhexanoate (Sn(Oct)₂)",
    "role_label": "catalyst",
    "role": "Classic catalyst for lactide ROP; forms the active tin alkoxide with an alcohol co-initiator.",
    "smiles": "CCCCC(CC)C(=O)[O-].CCCCC(CC)C(=O)[O-].[Sn+2]",
    "cid": 9318,
    "inchikey": "KSBAEPSJVUENNK-UHFFFAOYSA-L",
    "routes": [
      "pla"
    ],
    "ref": "kowalski2000"
  },
  {
    "id": "r-3hb",
    "name": "(R)-3-Hydroxybutanoic acid",
    "role_label": "monomer",
    "role": "Hydroxy acid of PHB; bacteria polymerise it from (R)-3-hydroxybutyryl-CoA.",
    "smiles": "C[C@@H](O)CC(=O)O",
    "cid": 92135,
    "inchikey": "WHBMMWSBFZVSSR-GSVOUGTGSA-N",
    "routes": [
      "pha"
    ],
    "ref": "sudesh2000"
  },
  {
    "id": "phb-ru",
    "name": "Poly[(R)-3-hydroxybutyrate] (PHB)",
    "role_label": "repeat unit",
    "role": "Repeat unit of PHB. Hydrolysis returns (R)-3-hydroxybutanoic acid.",
    "smiles": "*O[C@H](C)CC(*)=O",
    "hydrolysis": [
      "r-3hb"
    ],
    "routes": [
      "pha"
    ],
    "ref": "sudesh2000"
  },
  {
    "id": "3hv",
    "name": "3-Hydroxyvaleric acid",
    "role_label": "monomer",
    "role": "Hydroxy acid of the HV comonomer unit in PHBV (stereocentre not specified here).",
    "smiles": "CCC(O)CC(=O)O",
    "cid": 107802,
    "inchikey": "REKYPYSUBKSCAT-UHFFFAOYSA-N",
    "routes": [
      "pha"
    ],
    "ref": "bugnicourt2014"
  },
  {
    "id": "4hb",
    "name": "4-Hydroxybutanoic acid",
    "role_label": "monomer",
    "role": "Hydroxy acid of the 4HB unit in P3HB4HB copolymers.",
    "smiles": "OCCCC(=O)O",
    "cid": 10413,
    "inchikey": "SJZRECIVHVDYJC-UHFFFAOYSA-N",
    "routes": [
      "pha"
    ],
    "ref": "chen2009"
  },
  {
    "id": "3hhx",
    "name": "3-Hydroxyhexanoic acid",
    "role_label": "monomer",
    "role": "Hydroxy acid of the HHx unit in PHBHHx; its propyl side chain lowers crystallinity.",
    "smiles": "CCCC(O)CC(=O)O",
    "cid": 151492,
    "inchikey": "HPMGFDVTYHWBAG-UHFFFAOYSA-N",
    "routes": [
      "pha"
    ],
    "ref": "noda2004"
  },
  {
    "id": "hmf",
    "name": "5-Hydroxymethylfurfural (HMF)",
    "role_label": "feedstock",
    "role": "Sugar-derived platform chemical; oxidation gives FDCA.",
    "smiles": "O=Cc1ccc(CO)o1",
    "cid": 237332,
    "inchikey": "NOEGNKMFWQHSLB-UHFFFAOYSA-N",
    "routes": [
      "pef"
    ],
    "ref": "vanputten2013"
  },
  {
    "id": "fdca",
    "name": "2,5-Furandicarboxylic acid (FDCA)",
    "role_label": "monomer",
    "role": "Diacid of PEF and other furanoate polyesters.",
    "smiles": "OC(=O)c1ccc(o1)C(=O)O",
    "cid": 76720,
    "inchikey": "CHTHALBTIRVDBM-UHFFFAOYSA-N",
    "routes": [
      "pef"
    ],
    "ref": "sousa2015"
  },
  {
    "id": "fdme",
    "name": "Dimethyl 2,5-furandicarboxylate (FDME)",
    "role_label": "monomer",
    "role": "Diester alternative to FDCA for transesterification routes to PEF.",
    "smiles": "COC(=O)c1ccc(o1)C(=O)OC",
    "cid": 303530,
    "inchikey": "UWQOPFRNDNVUOA-UHFFFAOYSA-N",
    "routes": [
      "pef"
    ],
    "ref": "sousa2015"
  },
  {
    "id": "eg",
    "name": "Ethylene glycol (MEG)",
    "role_label": "monomer",
    "role": "Diol of PEF and PET; can be fossil- or bio-based.",
    "smiles": "OCCO",
    "cid": 174,
    "inchikey": "LYCAIKOWRPUZTN-UHFFFAOYSA-N",
    "routes": [
      "pef",
      "scope-review"
    ],
    "ref": "eerhart2012"
  },
  {
    "id": "pdo",
    "name": "1,3-Propanediol",
    "role_label": "monomer",
    "role": "Diol of poly(trimethylene furanoate) (PTF).",
    "smiles": "OCCCO",
    "cid": 10442,
    "inchikey": "YPFDHNVEDLHUCE-UHFFFAOYSA-N",
    "routes": [
      "pef"
    ],
    "ref": "sousa2015"
  },
  {
    "id": "pef-ru",
    "name": "Poly(ethylene 2,5-furandicarboxylate) (PEF)",
    "role_label": "repeat unit",
    "role": "Repeat unit of PEF. Hydrolysis gives ethylene glycol and FDCA.",
    "smiles": "*OCCOC(=O)c1ccc(o1)C(*)=O",
    "hydrolysis": [
      "eg",
      "fdca"
    ],
    "routes": [
      "pef"
    ],
    "ref": "burgess2014"
  },
  {
    "id": "tpa",
    "name": "Terephthalic acid",
    "role_label": "monomer",
    "role": "Fossil/drop-in benchmark: the PET diacid that FDCA replaces in PEF.",
    "benchmark": true,
    "smiles": "OC(=O)c1ccc(cc1)C(=O)O",
    "cid": 7489,
    "inchikey": "KKEYFWRCBNTPAC-UHFFFAOYSA-N",
    "routes": [
      "pef",
      "scope-review"
    ],
    "ref": "burgess2014"
  },
  {
    "id": "succinic",
    "name": "Succinic acid",
    "role_label": "monomer",
    "role": "Diacid of PBS and PBSA; available from fermentation or fossil routes.",
    "smiles": "OC(=O)CCC(=O)O",
    "cid": 1110,
    "inchikey": "KDYFGRWQOYBRFD-UHFFFAOYSA-N",
    "routes": [
      "bio-polyesters"
    ],
    "ref": "xu2010"
  },
  {
    "id": "bdo",
    "name": "1,4-Butanediol",
    "role_label": "monomer",
    "role": "Diol of PBS and PBAT.",
    "smiles": "OCCCCO",
    "cid": 8064,
    "inchikey": "WERYXYBDKMZEQL-UHFFFAOYSA-N",
    "routes": [
      "bio-polyesters"
    ],
    "ref": "xu2010"
  },
  {
    "id": "adipic",
    "name": "Adipic acid",
    "role_label": "monomer",
    "role": "Aliphatic diacid of PBAT and PBSA.",
    "smiles": "OC(=O)CCCCC(=O)O",
    "cid": 196,
    "inchikey": "WNLRTRBMVRJNCN-UHFFFAOYSA-N",
    "routes": [
      "bio-polyesters"
    ],
    "ref": "jian2020"
  },
  {
    "id": "pbs-ru",
    "name": "Poly(butylene succinate) (PBS)",
    "role_label": "repeat unit",
    "role": "Repeat unit of PBS. Hydrolysis gives 1,4-butanediol and succinic acid.",
    "smiles": "*OCCCCOC(=O)CCC(*)=O",
    "hydrolysis": [
      "bdo",
      "succinic"
    ],
    "routes": [
      "bio-polyesters"
    ],
    "ref": "xu2010"
  },
  {
    "id": "isosorbide",
    "name": "Isosorbide",
    "role_label": "monomer",
    "role": "Rigid, sugar-derived bicyclic diol (1,4:3,6-dianhydro-D-glucitol) for polycarbonates and polyesters.",
    "smiles": "O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@H]12",
    "cid": 12597,
    "inchikey": "KLDXJTOLSGUMSJ-JGWLITMVSA-N",
    "routes": [
      "bio-polyesters",
      "polycarbonates"
    ],
    "ref": "fenouillot2010"
  },
  {
    "id": "mbl",
    "name": "α-Methylene-γ-butyrolactone",
    "role_label": "monomer",
    "role": "Exo-methylene lactone studied as a monomer for chemically recyclable polymers.",
    "smiles": "C=C1CCOC1=O",
    "cid": 68352,
    "inchikey": "GSLDEZOOOSBFGP-UHFFFAOYSA-N",
    "routes": [
      "bio-polyesters"
    ],
    "ref": "coates2020"
  },
  {
    "id": "aua",
    "name": "11-Aminoundecanoic acid",
    "role_label": "monomer",
    "role": "Castor-derived amino acid monomer of PA11.",
    "smiles": "NCCCCCCCCCCC(=O)O",
    "cid": 17083,
    "inchikey": "GUOSQNAUYHMCRU-UHFFFAOYSA-N",
    "routes": [
      "polyamides"
    ],
    "ref": "winnacker2016"
  },
  {
    "id": "pa11-ru",
    "name": "Polyamide 11",
    "role_label": "repeat unit",
    "role": "Repeat unit of PA11. Hydrolysis returns 11-aminoundecanoic acid.",
    "smiles": "*NCCCCCCCCCCC(*)=O",
    "hydrolysis": [
      "aua"
    ],
    "routes": [
      "polyamides"
    ],
    "ref": "winnacker2016"
  },
  {
    "id": "ricinoleic",
    "name": "Ricinoleic acid",
    "role_label": "feedstock",
    "role": "Main fatty acid of castor oil; source of PA11 and sebacic-acid chemistry and of bio-polyols.",
    "smiles": "CCCCCC[C@@H](O)C/C=C\\CCCCCCCC(=O)O",
    "cid": 643684,
    "inchikey": "WBHHMMIMDMUBKC-QJWNTBNXSA-N",
    "routes": [
      "polyamides",
      "polyurethanes"
    ],
    "ref": "winnacker2016"
  },
  {
    "id": "sebacic",
    "name": "Sebacic acid",
    "role_label": "monomer",
    "role": "C10 diacid for PA610 and PA1010.",
    "smiles": "OC(=O)CCCCCCCCC(=O)O",
    "cid": 5192,
    "inchikey": "CXMXRPHRNRROMY-UHFFFAOYSA-N",
    "routes": [
      "polyamides"
    ],
    "ref": "winnacker2016"
  },
  {
    "id": "cadaverine",
    "name": "Cadaverine (1,5-diaminopentane)",
    "role_label": "monomer",
    "role": "Bio-produced diamine for PA 5.X polyamides.",
    "smiles": "NCCCCCN",
    "cid": 273,
    "inchikey": "VHRGRCVQAFMJIZ-UHFFFAOYSA-N",
    "routes": [
      "polyamides"
    ],
    "ref": "kind2011"
  },
  {
    "id": "dmda",
    "name": "1,10-Decanediamine",
    "role_label": "monomer",
    "role": "C10 diamine for PA1010 and PA10.X polyamides.",
    "smiles": "NCCCCCCCCCCN",
    "cid": 1317,
    "inchikey": "YQLZOAVZWJBZSY-UHFFFAOYSA-N",
    "routes": [
      "polyamides"
    ],
    "ref": "winnacker2016"
  },
  {
    "id": "po",
    "name": "Propylene oxide",
    "role_label": "monomer",
    "role": "Epoxide comonomer with CO₂ for poly(propylene carbonate) (stereocentre not specified).",
    "smiles": "CC1CO1",
    "cid": 6378,
    "inchikey": "GOOHAUXETOMSMM-UHFFFAOYSA-N",
    "routes": [
      "polycarbonates"
    ],
    "ref": "grignard2019"
  },
  {
    "id": "limonene",
    "name": "(R)-Limonene",
    "role_label": "feedstock",
    "role": "Citrus terpene; its oxide copolymerises with CO₂ to poly(limonene carbonate).",
    "smiles": "CC1=CC[C@@H](CC1)C(=C)C",
    "cid": 440917,
    "inchikey": "XMGQYMWWDOXHJM-JTQLQIEISA-N",
    "routes": [
      "polycarbonates"
    ],
    "ref": "byrne2004"
  },
  {
    "id": "glycerol-carbonate",
    "name": "Glycerol carbonate",
    "role_label": "monomer",
    "role": "Five-membered cyclic carbonate; amines open it to hydroxyurethanes (NIPU).",
    "smiles": "O=C1OCC(CO)O1",
    "cid": 97944,
    "inchikey": "JFMGYULNQJPJCY-UHFFFAOYSA-N",
    "routes": [
      "polyurethanes"
    ],
    "ref": "rokicki2015"
  },
  {
    "id": "pdi",
    "name": "Pentamethylene diisocyanate (PDI)",
    "role_label": "monomer",
    "role": "Aliphatic diisocyanate that can be made from bio-based cadaverine.",
    "smiles": "O=C=NCCCCCN=C=O",
    "cid": 11948526,
    "inchikey": "DFPJRUKWEPYFJT-UHFFFAOYSA-N",
    "routes": [
      "polyurethanes"
    ],
    "ref": "rokicki2015"
  },
  {
    "id": "vanillin",
    "name": "Vanillin",
    "role_label": "feedstock",
    "role": "Lignin-derivable aromatic aldehyde; precursor of bio-based epoxy monomers.",
    "smiles": "COc1cc(C=O)ccc1O",
    "cid": 1183,
    "inchikey": "MWOOGOJBHIARFG-UHFFFAOYSA-N",
    "routes": [
      "thermosets"
    ],
    "ref": "fache2015"
  },
  {
    "id": "itaconic",
    "name": "Itaconic acid",
    "role_label": "monomer",
    "role": "Fermentation-derived unsaturated diacid for curable polyesters.",
    "smiles": "C=C(CC(=O)O)C(=O)O",
    "cid": 811,
    "inchikey": "LVHBHZANLOWSRM-UHFFFAOYSA-N",
    "routes": [
      "thermosets"
    ],
    "ref": "robert2016"
  },
  {
    "id": "furfuryl-alcohol",
    "name": "Furfuryl alcohol",
    "role_label": "monomer",
    "role": "Furan monomer for furan resins and Diels–Alder networks.",
    "smiles": "OCc1ccco1",
    "cid": 7361,
    "inchikey": "XPFVYQJUAUNWIW-UHFFFAOYSA-N",
    "routes": [
      "thermosets"
    ],
    "ref": "gandini2016"
  },
  {
    "id": "cardanol",
    "name": "Cardanol (triene component)",
    "role_label": "representative unit",
    "role": "Representative: cardanol from cashew nut shell liquid is a mixture; shown is the C15 triene component.",
    "smiles": "C=CC/C=C\\C/C=C\\CCCCCCCC1=CC(=CC=C1)O",
    "cid": 11266523,
    "inchikey": "JOLVYUIAMRUBRK-UTOQUPLUSA-N",
    "routes": [
      "thermosets"
    ],
    "ref": "auvergne2014"
  },
  {
    "id": "beta-glucose",
    "name": "β-D-Glucopyranose",
    "role_label": "representative unit",
    "role": "Representative unit of cellulose (β-1,4-linked D-glucose); not the polymer itself.",
    "smiles": "OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O",
    "cid": 64689,
    "inchikey": "WQZGKKKJIJFFOK-VFUOTHLCSA-N",
    "routes": [
      "natural-polymers"
    ],
    "ref": "klemm2005"
  },
  {
    "id": "alpha-glucose",
    "name": "α-D-Glucopyranose",
    "role_label": "representative unit",
    "role": "Representative unit of starch (α-linked D-glucose); not the polymer itself.",
    "smiles": "OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O",
    "cid": 79025,
    "inchikey": "WQZGKKKJIJFFOK-DVKNGEFBSA-N",
    "routes": [
      "natural-polymers"
    ],
    "ref": "zhang2014"
  },
  {
    "id": "coniferyl",
    "name": "Coniferyl alcohol",
    "role_label": "representative unit",
    "role": "Representative lignin monolignol (G unit); lignin itself has no single defined structure.",
    "smiles": "OC/C=C/c1ccc(O)c(OC)c1",
    "cid": 1549095,
    "inchikey": "JMFRWRFFLBVWSI-NSCUHMNNSA-N",
    "routes": [
      "natural-polymers",
      "polyurethanes"
    ],
    "ref": "upton2016"
  },
  {
    "id": "glucosamine",
    "name": "D-Glucosamine",
    "role_label": "representative unit",
    "role": "Representative unit of chitosan (anomeric centre unspecified); not the polymer itself.",
    "smiles": "OC[C@H]1OC(O)[C@H](N)[C@@H](O)[C@@H]1O",
    "cid": 439213,
    "inchikey": "MSWZFWKMSRAUBD-IVMDWMLBSA-N",
    "routes": [
      "natural-polymers"
    ],
    "ref": "rinaudo2006"
  },
  {
    "id": "l-lysine",
    "name": "L-Lysine",
    "role_label": "representative unit",
    "role": "Representative amino acid for protein-based plastics; proteins are not drawn as full structures.",
    "smiles": "NCCCC[C@H](N)C(=O)O",
    "cid": 5962,
    "inchikey": "KDXKERNSBIXSRK-YFKPBYRVSA-N",
    "routes": [
      "natural-polymers"
    ],
    "ref": "verbeek2010"
  }
]