ENTRY C06165 Compound NAME Macarpine FORMULA C22H18NO6 EXACT_MASS 392.1134 MOL_WEIGHT 392.38 REACTION R04768 PATHWAY map00950 Isoquinoline alkaloid biosynthesis map01063 Biosynthesis of alkaloids derived from shikimate pathway map01100 Metabolic pathways map01110 Biosynthesis of secondary metabolites ENZYME 1.5.3.12 BRITE Phytochemical compounds [BR:br08003] Alkaloids Alkaloids derived from tyrosine Isoquinoline alkaloids C06165 Macarpine DBLINKS CAS: 23594-80-1 PubChem: 8420 ChEBI: 17101 KNApSAcK: C00001883 NIKKAJI: J361.279A ATOM 29 1 C8y C 25.3425 -20.5131 2 C8y C 24.1327 -21.2094 3 C8y C 26.5592 -21.2355 4 C8x C 25.3662 -19.1204 5 C8y C 24.1766 -22.6045 6 C8y C 22.9183 -20.4893 7 C8y C 27.7690 -20.5510 8 N5y N 26.5474 -22.6401 #+ 9 C8y C 26.5853 -18.4359 10 C8x C 25.3235 -23.3271 11 C8x C 21.6966 -21.1976 12 O2a O 22.8576 -19.0943 13 C8y C 27.7928 -19.1490 14 C8x C 28.9622 -21.2616 15 C1a C 27.7641 -23.3390 16 C1a C 21.7109 -18.3930 17 C8x C 29.0002 -18.4740 18 C8y C 30.1790 -20.5676 19 C8y C 30.2027 -19.1726 20 O2x O 31.4934 -21.0241 21 O2x O 31.5313 -18.7734 22 C1x C 32.3347 -19.9094 23 C8y C 22.8929 -23.3187 24 C8y C 21.6847 -22.6021 25 O2x O 20.6299 -23.5297 26 C1x C 21.1862 -24.8193 27 O2x O 22.5847 -24.6890 28 O2a O 26.6008 -17.0376 29 C1a C 25.3974 -16.3251 BOND 34 1 3 8 1 2 4 9 2 3 5 23 1 4 5 10 1 5 6 11 2 6 6 12 1 7 7 13 2 8 7 14 1 9 8 15 1 10 12 16 1 11 13 17 1 12 14 18 2 13 17 19 2 14 18 20 1 15 19 21 1 16 20 22 1 17 8 10 2 18 9 13 1 19 11 24 1 20 18 19 1 21 21 22 1 22 1 2 1 23 1 3 2 24 1 4 1 25 2 5 2 26 23 24 2 27 24 25 1 28 25 26 1 29 26 27 1 30 27 23 1 31 2 6 1 32 9 28 1 33 3 7 1 34 28 29 1 /// ENTRY C06167 Compound NAME 1,2-Dehydroreticuline; 1,2-Dehydroreticulinium; 3,4-Dihydro-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-(methyl-14C)-isoquinolinium FORMULA C19H22NO4 EXACT_MASS 328.1549 MOL_WEIGHT 328.38 REACTION R03833 R04695 PATHWAY map00950 Isoquinoline alkaloid biosynthesis map01100 Metabolic pathways map01110 Biosynthesis of secondary metabolites MODULE M00944 Morphine biosynthesis, (S)-reticuline => morphine ENZYME 1.5.1.27 1.14.19.54 DBLINKS CAS: 16202-17-8 PubChem: 8421 ChEBI: 18363 KNApSAcK: C00027111 NIKKAJI: J471.975A ATOM 24 1 C8y C 27.6940 -18.3004 2 C2y C 28.8994 -17.6254 3 C8y C 27.6883 -19.6903 4 C8x C 26.5059 -17.6025 5 C1b C 28.8994 -16.2470 6 N2y N 30.0990 -18.3119 #+ 7 C8x C 26.4885 -20.3767 8 C1x C 28.8879 -20.3883 9 C8y C 25.3004 -18.2829 10 C8y C 30.0990 -15.5549 11 C1x C 30.0934 -19.6962 12 C1a C 31.6384 -17.2744 13 C8y C 25.2889 -19.6673 14 O1a O 24.1066 -17.5910 15 C8x C 31.2930 -16.2414 16 C8x C 30.0990 -14.1765 17 O2a O 24.0835 -20.3537 18 C8y C 32.4812 -15.5493 19 C8x C 31.2872 -13.4901 20 C1a C 22.8839 -19.6557 21 C8y C 32.4812 -14.1707 22 O1a O 33.6635 -16.2645 23 O2a O 33.6751 -13.5016 24 C1a C 34.8631 -14.2053 BOND 26 1 1 2 1 2 1 3 1 3 1 4 2 4 2 5 1 5 2 6 2 6 3 7 2 7 3 8 1 8 4 9 1 9 5 10 1 10 6 11 1 11 6 12 1 12 7 13 1 13 9 14 1 14 10 15 2 15 10 16 1 16 13 17 1 17 15 18 1 18 16 19 2 19 17 20 1 20 18 21 2 21 18 22 1 22 21 23 1 23 23 24 1 24 8 11 1 25 9 13 2 26 19 21 1 /// ENTRY C06161 Compound NAME (S)-Coclaurine; Coclaurine; (S)-1,2,3,4-Tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-7-isoquinolinol; 1-(p-Hydroxybenzyl)-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline FORMULA C17H19NO3 EXACT_MASS 285.1365 MOL_WEIGHT 285.34 REACTION R04692 R05123 R05210 R08456 PATHWAY map00950 Isoquinoline alkaloid biosynthesis map01063 Biosynthesis of alkaloids derived from shikimate pathway map01100 Metabolic pathways map01110 Biosynthesis of secondary metabolites MODULE M00943 Reticuline biosynthesis, dopamine + 4HPAA => (S)-reticuline ENZYME 1.14.19.66 2.1.1.115 2.1.1.128 2.1.1.140 BRITE Phytochemical compounds [BR:br08003] Alkaloids Alkaloids derived from tyrosine Isoquinoline alkaloids C06161 (S)-Coclaurine DBLINKS CAS: 486-39-5 PubChem: 8417 ChEBI: 15950 KNApSAcK: C00025812 NIKKAJI: J6.009G ATOM 21 1 C8y C 25.8543 -22.0022 2 C1y C 27.0719 -21.3032 3 C8y C 25.8486 -23.4063 4 C8x C 24.6426 -21.2973 5 C1b C 27.0778 -19.9050 6 N1x N 28.2838 -22.0138 7 C8x C 24.6426 -24.0995 8 C1x C 27.0603 -24.1054 9 C8y C 23.4309 -22.0022 10 C8y C 28.2955 -19.2116 11 C1x C 28.2779 -23.4121 12 C8y C 23.4309 -23.4063 13 O1a O 22.2190 -21.2973 14 C8x C 28.2955 -17.8133 15 C8x C 29.5131 -19.9107 16 O2a O 22.2190 -24.0995 17 C8x C 29.5131 -17.1085 18 C8x C 30.7248 -19.2116 19 C1a C 21.0130 -23.4063 20 C8y C 30.7248 -17.8133 21 O1a O 31.9308 -17.1085 BOND 23 1 1 2 1 2 1 3 2 3 1 4 1 4 2 5 1 #Down 5 2 6 1 6 3 7 1 7 3 8 1 8 4 9 2 9 5 10 1 10 6 11 1 11 7 12 2 12 9 13 1 13 10 14 1 14 10 15 2 15 12 16 1 16 14 17 2 17 15 18 1 18 16 19 1 19 17 20 1 20 20 21 1 21 8 11 1 22 9 12 1 23 18 20 2 /// ENTRY C06160 Compound NAME (S)-Norcoclaurine; 6,7-Dihydroxy-(1S)-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline FORMULA C16H17NO3 EXACT_MASS 271.1208 MOL_WEIGHT 271.31 REACTION R04305 R05123 PATHWAY map00950 Isoquinoline alkaloid biosynthesis map01063 Biosynthesis of alkaloids derived from shikimate pathway map01100 Metabolic pathways map01110 Biosynthesis of secondary metabolites MODULE M00943 Reticuline biosynthesis, dopamine + 4HPAA => (S)-reticuline ENZYME 2.1.1.128 3.5.99.14 BRITE Phytochemical compounds [BR:br08003] Alkaloids Alkaloids derived from tyrosine Isoquinoline alkaloids C06160 (S)-Norcoclaurine DBLINKS CAS: 22672-77-1 PubChem: 8416 ChEBI: 17729 KNApSAcK: C00034613 NIKKAJI: J444.134F ATOM 20 1 C8y C 24.8082 -20.6392 2 C1y C 26.0226 -19.9385 3 C8y C 24.8023 -22.0462 4 C8x C 23.5937 -19.9328 5 C1b C 26.0285 -18.5432 6 N1x N 27.2371 -20.6508 7 C8x C 23.5937 -22.7411 8 C1x C 26.0109 -22.7468 9 C8y C 22.3735 -20.6392 10 C8y C 27.2428 -17.8483 11 C1x C 27.2312 -22.0579 12 C8y C 22.3735 -22.0462 13 O1a O 21.1649 -19.9445 14 C8x C 28.4457 -18.5549 15 C8x C 27.2428 -16.4530 16 O1a O 21.1649 -22.7468 17 C8x C 29.6600 -17.8600 18 C8x C 28.4572 -15.7640 19 C8y C 29.6658 -16.4647 20 O1a O 30.8743 -15.7700 BOND 22 1 1 2 1 2 1 3 2 3 1 4 1 4 2 5 1 #Down 5 2 6 1 6 3 7 1 7 3 8 1 8 4 9 2 9 5 10 1 10 6 11 1 11 7 12 2 12 9 13 1 13 10 14 2 14 10 15 1 15 12 16 1 16 14 17 1 17 15 18 2 18 17 19 2 19 19 20 1 20 8 11 1 21 9 12 1 22 18 19 1 /// ENTRY C06163 Compound NAME (S)-cis-N-Methylstylopine FORMULA C20H20NO4 EXACT_MASS 338.1392 MOL_WEIGHT 338.38 REACTION R04691 R04700 PATHWAY map00950 Isoquinoline alkaloid biosynthesis map01100 Metabolic pathways map01110 Biosynthesis of secondary metabolites MODULE M00945 Sanguinarine biosynthesis, (S)-reticuline => sanguinarine ENZYME 1.14.14.97 2.1.1.122 BRITE Phytochemical compounds [BR:br08003] Alkaloids Alkaloids derived from tyrosine Isoquinoline alkaloids C06163 (S)-cis-N-methylstylopine DBLINKS PubChem: 8419 ChEBI: 444 KNApSAcK: C00026083 C00026110 PDB-CCD: SYT NIKKAJI: J1.767.334C ATOM 25 1 C8y C 12.8800 -13.7900 2 C8y C 12.8800 -15.1900 3 C8x C 14.0700 -15.8900 4 C8y C 15.3300 -15.1900 5 C8y C 15.3300 -13.7900 6 C8x C 14.0700 -13.0900 7 O2x O 11.5500 -13.3700 8 C1x C 10.7100 -14.4900 9 O2x O 11.5500 -15.6100 10 C1x C 16.5200 -15.8900 11 C1x C 17.7100 -15.1900 12 N2y N 17.7100 -13.7900 #+ 13 C1y C 16.5200 -13.0900 14 C1x C 18.9700 -13.0900 15 C8y C 18.9700 -11.6900 16 C8y C 17.7100 -10.9900 17 C1x C 16.5200 -11.6900 18 C1a C 18.9700 -14.4900 19 C8y C 20.1600 -10.9900 20 C8y C 20.1600 -9.5900 21 C8x C 18.9700 -8.8900 22 C8x C 17.7100 -9.5900 23 O2x O 21.4900 -11.4100 24 C1x C 22.3300 -10.2900 25 O2x O 21.4900 -9.1700 BOND 30 1 1 2 2 2 2 3 1 3 3 4 2 4 4 5 1 5 5 6 2 6 1 6 1 7 1 7 1 8 7 8 1 9 8 9 1 10 2 9 1 11 4 10 1 12 10 11 1 13 11 12 1 14 12 13 1 15 5 13 1 16 12 14 1 17 14 15 1 18 15 16 2 19 16 17 1 20 13 17 1 21 12 18 1 #Up 22 15 19 1 23 19 20 2 24 20 21 1 25 21 22 2 26 16 22 1 27 19 23 1 28 23 24 1 29 24 25 1 30 20 25 1 /// ENTRY C06162 Compound NAME Sanguinarine FORMULA C20H14NO4 EXACT_MASS 332.0923 MOL_WEIGHT 332.33 REACTION R04703 R10798 R10799 PATHWAY map00950 Isoquinoline alkaloid biosynthesis map01100 Metabolic pathways MODULE M00945 Sanguinarine biosynthesis, (S)-reticuline => sanguinarine ENZYME 1.3.1.107 1.3.3.8 1.5.3.12 BRITE Phytochemical compounds [BR:br08003] Alkaloids Alkaloids derived from tyrosine Isoquinoline alkaloids C06162 Sanguinarine Natural toxins [BR:br08009] Phytotoxins Alkaloids Isoquinoline alkaloids C06162 Sanguinarine Secondary metabolites in pathway maps [br08011.html] Biosynthetic pathways and modules of secondary metabolites C06162 DBLINKS CAS: 2447-54-3 PubChem: 8418 ChEBI: 17183 KNApSAcK: C00001917 C00024663 PDB-CCD: SAU NIKKAJI: J7.576K ATOM 25 1 C8x C 19.6000 -8.4000 2 C8y C 19.6000 -9.8000 3 C8y C 20.8124 -10.5000 4 C8y C 22.0249 -9.8000 5 C8y C 22.0249 -8.4000 6 C8x C 20.8124 -7.7000 7 C8x C 23.2373 -10.5000 8 N5y N 24.4497 -9.8000 #+ 9 C8y C 24.4497 -8.4000 10 C8y C 23.2373 -7.7000 11 C8y C 25.6622 -7.7000 12 C8y C 25.6622 -6.3000 13 C8x C 24.4497 -5.6000 14 C8x C 23.2373 -6.3000 15 C8x C 26.8746 -8.4000 16 C8y C 28.0870 -7.7000 17 C8y C 28.0870 -6.3000 18 C8x C 26.8746 -5.6000 19 O2x O 18.5596 -10.7368 20 C1x C 19.1290 -12.0158 21 O2x O 20.5214 -11.8694 22 O2x O 29.4185 -8.1326 23 C1x C 30.2414 -7.0000 24 O2x O 29.4185 -5.8674 25 C1a C 25.6473 -10.4915 BOND 30 1 1 2 2 2 2 3 1 3 3 4 2 4 4 5 1 5 5 6 2 6 1 6 1 7 4 7 1 8 7 8 2 9 8 9 1 10 9 10 2 11 5 10 1 12 9 11 1 13 11 12 2 14 12 13 1 15 13 14 2 16 10 14 1 17 11 15 1 18 15 16 2 19 16 17 1 20 17 18 2 21 12 18 1 22 2 19 1 23 19 20 1 24 20 21 1 25 3 21 1 26 16 22 1 27 22 23 1 28 23 24 1 29 17 24 1 30 8 25 1 /// ENTRY C05587 Compound NAME 3-Methoxytyramine FORMULA C9H13NO2 EXACT_MASS 167.0946 MOL_WEIGHT 167.20 REACTION R04301 R04890 R08831 PATHWAY map00350 Tyrosine metabolism map00965 Betalain biosynthesis map01063 Biosynthesis of alkaloids derived from shikimate pathway map01100 Metabolic pathways map04728 Dopaminergic synapse ENZYME 1.4.3.4 2.1.1.6 DBLINKS CAS: 554-52-9 PubChem: 7912 ChEBI: 1582 KNApSAcK: C00042132 NIKKAJI: J31.076J ATOM 12 1 C8y C 24.1582 -17.6274 2 C8x C 25.3542 -16.9412 3 C8y C 24.1624 -19.0344 4 C8y C 26.6240 -17.6548 5 C8x C 25.3626 -19.7552 6 C8x C 26.6282 -19.0618 7 C1b C 27.8124 -16.9400 8 C1b C 29.0249 -17.6400 9 N1a N 30.2373 -16.9400 10 O2a O 22.9450 -16.9272 11 O1a O 22.9332 -19.7325 12 C1a C 21.7385 -17.6241 BOND 12 1 1 2 2 2 1 3 1 3 2 4 1 4 3 5 2 5 4 6 2 6 5 6 1 7 4 7 1 8 7 8 1 9 8 9 1 10 1 10 1 11 3 11 1 12 10 12 1 /// ENTRY C05584 Compound NAME 3-Methoxy-4-hydroxymandelate; Vanillylmandelic acid FORMULA C9H10O5 EXACT_MASS 198.0528 MOL_WEIGHT 198.17 REACTION R04887 R04891 R04892 PATHWAY map00350 Tyrosine metabolism map01100 Metabolic pathways ENZYME 1.2.1.5 2.1.1.6 DBLINKS CAS: 55-10-7 PubChem: 7910 ChEBI: 20106 27622 NIKKAJI: J27.583B ATOM 14 1 C8x C 22.1900 -19.8100 2 C8y C 22.1900 -21.2100 3 C8y C 23.4024 -21.9100 4 C8x C 24.6149 -21.2100 5 C8y C 24.6149 -19.8100 6 C8x C 23.4024 -19.1100 7 C1c C 25.8524 -19.1100 8 C6a C 27.0649 -19.8100 9 O6a O 28.2773 -19.1100 10 O1a O 25.8586 -17.7103 11 O6a O 27.0649 -21.2098 12 O2a O 23.4024 -23.3098 13 C1a C 22.1732 -24.0197 14 O1a O 20.9776 -21.9100 BOND 14 1 1 2 2 2 2 3 1 3 3 4 2 4 4 5 1 5 5 6 2 6 1 6 1 7 5 7 1 8 7 8 1 9 8 9 1 10 7 10 1 11 8 11 2 12 3 12 1 13 12 13 1 14 2 14 1 /// ENTRY C05585 Compound NAME Gentisate aldehyde; 2,5-Dihydroxybenzaldehyde FORMULA C7H6O3 EXACT_MASS 138.0317 MOL_WEIGHT 138.12 REACTION R02518 R02520 R02655 R02657 PATHWAY map00350 Tyrosine metabolism map01100 Metabolic pathways map01120 Microbial metabolism in diverse environments ENZYME 1.2.1.29 1.2.3.1 1.13.12.- 4.1.1.- DBLINKS PubChem: 7911 ChEBI: 28508 NIKKAJI: J7.451I ATOM 10 1 C8x C 17.8500 -23.0300 2 C8y C 17.8500 -24.4300 3 C8x C 19.0624 -25.1300 4 C8x C 20.2749 -24.4300 5 C8y C 20.2749 -23.0300 6 C8y C 19.0624 -22.3300 7 O1a O 16.6376 -25.1300 8 O1a O 21.5060 -22.3190 9 C4a C 19.0624 -20.9302 10 O4a O 17.8332 -20.2203 BOND 10 1 1 2 2 2 2 3 1 3 3 4 2 4 4 5 1 5 5 6 2 6 1 6 1 7 2 7 1 8 5 8 1 9 6 9 1 10 9 10 2 /// ENTRY C00099 Compound NAME beta-Alanine; 3-Aminopropionic acid; 3-Aminopropanoate FORMULA C3H7NO2 EXACT_MASS 89.0477 MOL_WEIGHT 89.09 REMARK Same as: D07561 REACTION R00489 R00904 R00905 R00906 R00907 R00908 R00909 R00910 R00911 R00912 R00913 R00914 R00915 R00916 R00917 R01164 R01166 R02473 R02474 R02741 R03286 R03288 R03935 R09379 R09648 R10821 PATHWAY map00240 Pyrimidine metabolism map00410 beta-Alanine metabolism map00640 Propanoate metabolism map00770 Pantothenate and CoA biosynthesis map01100 Metabolic pathways map01110 Biosynthesis of secondary metabolites map01240 Biosynthesis of cofactors map04080 Neuroactive ligand-receptor interaction map04974 Protein digestion and absorption MODULE M00046 Pyrimidine degradation, uracil => beta-alanine, thymine => 3-aminoisobutanoate M00119 Pantothenate biosynthesis, valine/L-aspartate => pantothenate M00913 Pantothenate biosynthesis, 2-oxoisovalerate/spermine => pantothenate ENZYME 1.2.1.3 1.2.1.5 1.2.1.19 1.5.1.26 2.6.1.18 2.6.1.19 2.6.1.55 2.6.1.120 2.8.3.- 3.4.13.4 3.4.13.5 3.4.13.18 3.4.13.20 3.5.1.6 3.5.1.21 3.5.1.22 3.5.1.100 3.5.3.17 4.1.1.11 4.1.1.15 6.3.2.1 6.3.2.11 6.3.2.23 6.3.2.36 6.3.2.44 BRITE Compounds with biological roles [BR:br08001] Peptides Amino acids Other amino acids C00099 beta-Alanine Amines Biogenic amines C00099 beta-Alanine DBLINKS CAS: 107-95-9 PubChem: 3399 ChEBI: 16958 KNApSAcK: C00001333 PDB-CCD: BAL NIKKAJI: J4.070C ATOM 6 1 C1b C 25.6778 -16.8919 2 C6a C 24.4732 -16.1936 3 C1b C 26.8940 -16.1936 4 O6a O 23.2571 -16.8978 5 O6a O 24.4732 -14.7912 6 N1a N 28.1045 -16.8919 BOND 5 1 1 2 1 2 1 3 1 3 2 4 1 4 2 5 2 5 3 6 1 ///