data_I8E
# 
_chem_comp.id                                    I8E 
_chem_comp.name                                  Tetrahydrocannabivarin 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H26 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-dibenzo[b,d]pyran-1-ol; THCV; THV; O-4394; GWP42004" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2023-05-04 
_chem_comp.pdbx_modified_date                    2023-08-18 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        286.409 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     I8E 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        8SP8 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
I8E C1   C1  C 0 1 N N N 90.769 116.904 110.655 6.384  0.194  1.103  C1   I8E 1  
I8E C10  C2  C 0 1 N N N 85.195 116.828 119.074 -3.098 1.757  0.503  C10  I8E 2  
I8E C11  C3  C 0 1 N N N 85.416 115.611 119.917 -3.983 0.612  0.895  C11  I8E 3  
I8E C12  C4  C 0 1 N N N 85.754 114.353 119.136 -3.521 -0.702 0.254  C12  I8E 4  
I8E C13  C5  C 0 1 N N R 86.674 114.703 117.967 -2.002 -0.774 0.389  C13  I8E 5  
I8E C14  C6  C 0 1 N N N 87.308 113.523 117.230 -1.428 -2.114 -0.063 C14  I8E 6  
I8E C16  C7  C 0 1 Y N N 88.114 115.285 115.751 0.697  -0.979 -0.117 C16  I8E 7  
I8E C17  C8  C 0 1 Y N N 89.094 115.654 114.854 2.086  -1.054 -0.090 C17  I8E 8  
I8E C18  C9  C 0 1 N N N 86.360 112.801 116.286 -1.685 -2.310 -1.558 C18  I8E 9  
I8E C19  C10 C 0 1 N N N 88.004 112.530 118.142 -2.080 -3.250 0.729  C19  I8E 10 
I8E C2   C11 C 0 1 N N N 89.604 117.210 111.557 4.857  0.291  1.069  C2   I8E 11 
I8E C20  C12 C 0 1 N N N 84.643 118.028 119.784 -3.572 3.147  0.840  C20  I8E 12 
I8E C3   C13 C 0 1 N N N 89.965 117.120 113.019 4.357  -0.038 -0.339 C3   I8E 13 
I8E C4   C14 C 0 1 Y N N 88.863 116.674 113.948 2.853  0.057  -0.373 C4   I8E 14 
I8E C5   C15 C 0 1 Y N N 87.636 117.321 113.969 2.246  1.258  -0.687 C5   I8E 15 
I8E C6   C16 C 0 1 Y N N 86.655 116.948 114.874 0.862  1.342  -0.722 C6   I8E 16 
I8E C7   C17 C 0 1 Y N N 86.883 115.942 115.816 0.091  0.220  -0.441 C7   I8E 17 
I8E C8   C18 C 0 1 N N R 85.949 115.648 116.986 -1.403 0.316  -0.506 C8   I8E 18 
I8E C9   C19 C 0 1 N N N 85.478 116.836 117.775 -1.950 1.644  -0.099 C9   I8E 19 
I8E O15  O1  O 0 1 N N N 88.370 114.122 116.433 -0.020 -2.092 0.190  O15  I8E 20 
I8E O21  O2  O 0 1 N N N 85.417 117.480 114.701 0.262  2.521  -1.031 O21  I8E 21 
I8E H1A  H1  H 0 1 N N N 90.451 116.984 109.605 6.740  0.429  2.106  H1A  I8E 22 
I8E H1C  H2  H 0 1 N N N 91.580 117.621 110.848 6.690  -0.818 0.836  H1C  I8E 23 
I8E H1B  H3  H 0 1 N N N 91.127 115.883 110.853 6.809  0.902  0.392  H1B  I8E 24 
I8E H11B H4  H 0 0 N N N 86.246 115.819 120.608 -3.967 0.505  1.979  H11B I8E 25 
I8E H11A H5  H 0 0 N N N 84.498 115.421 120.493 -5.003 0.825  0.573  H11A I8E 26 
I8E H12A H6  H 0 0 N N N 84.828 113.903 118.750 -3.978 -1.546 0.771  H12A I8E 27 
I8E H12B H7  H 0 0 N N N 86.262 113.637 119.799 -3.801 -0.718 -0.799 H12B I8E 28 
I8E H13  H8  H 0 1 N N N 87.506 115.284 118.392 -1.720 -0.589 1.425  H13  I8E 29 
I8E H17  H9  H 0 1 N N N 90.046 115.145 114.859 2.568  -1.990 0.156  H17  I8E 30 
I8E H18C H10 H 0 0 N N N 85.547 112.339 116.865 -1.207 -1.506 -2.118 H18C I8E 31 
I8E H18B H11 H 0 0 N N N 85.937 113.521 115.570 -1.273 -3.268 -1.875 H18B I8E 32 
I8E H18A H12 H 0 0 N N N 86.910 112.021 115.740 -2.758 -2.296 -1.748 H18A I8E 33 
I8E H19A H13 H 0 0 N N N 88.685 113.067 118.818 -3.156 -3.242 0.556  H19A I8E 34 
I8E H19C H14 H 0 0 N N N 87.253 111.987 118.734 -1.666 -4.204 0.402  H19C I8E 35 
I8E H19B H15 H 0 0 N N N 88.578 111.815 117.535 -1.881 -3.112 1.792  H19B I8E 36 
I8E H2B  H16 H 0 1 N N N 89.251 118.230 111.343 4.432  -0.417 1.781  H2B  I8E 37 
I8E H2A  H17 H 0 1 N N N 88.798 116.491 111.348 4.551  1.303  1.336  H2A  I8E 38 
I8E H20C H18 H 0 0 N N N 84.489 117.787 120.846 -3.210 3.424  1.830  H20C I8E 39 
I8E H20B H19 H 0 0 N N N 85.353 118.864 119.697 -3.187 3.851  0.102  H20B I8E 40 
I8E H20A H20 H 0 0 N N N 83.683 118.313 119.330 -4.662 3.171  0.832  H20A I8E 41 
I8E H3B  H21 H 0 1 N N N 90.796 116.406 113.117 4.782  0.669  -1.050 H3B  I8E 42 
I8E H3A  H22 H 0 1 N N N 90.297 118.117 113.345 4.663  -1.050 -0.606 H3A  I8E 43 
I8E H5   H23 H 0 1 N N N 87.443 118.124 113.273 2.847  2.128  -0.905 H5   I8E 44 
I8E H8   H24 H 0 1 N N N 85.067 115.119 116.595 -1.713 0.118  -1.532 H8   I8E 45 
I8E H9   H25 H 0 1 N N N 85.360 117.770 117.246 -1.378 2.536  -0.312 H9   I8E 46 
I8E H21  H26 H 0 1 N N N 84.834 117.153 115.376 0.097  2.643  -1.976 H21  I8E 47 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
I8E C1  C2   SING N N 1  
I8E C2  C3   SING N N 2  
I8E C3  C4   SING N N 3  
I8E C4  C5   DOUB Y N 4  
I8E C4  C17  SING Y N 5  
I8E C5  C6   SING Y N 6  
I8E O21 C6   SING N N 7  
I8E C17 C16  DOUB Y N 8  
I8E C6  C7   DOUB Y N 9  
I8E C16 C7   SING Y N 10 
I8E C16 O15  SING N N 11 
I8E C7  C8   SING N N 12 
I8E C18 C14  SING N N 13 
I8E O15 C14  SING N N 14 
I8E C8  C9   SING N N 15 
I8E C8  C13  SING N N 16 
I8E C14 C13  SING N N 17 
I8E C14 C19  SING N N 18 
I8E C9  C10  DOUB N N 19 
I8E C13 C12  SING N N 20 
I8E C10 C20  SING N N 21 
I8E C10 C11  SING N N 22 
I8E C12 C11  SING N N 23 
I8E C1  H1A  SING N N 24 
I8E C1  H1C  SING N N 25 
I8E C1  H1B  SING N N 26 
I8E C11 H11B SING N N 27 
I8E C11 H11A SING N N 28 
I8E C12 H12A SING N N 29 
I8E C12 H12B SING N N 30 
I8E C13 H13  SING N N 31 
I8E C17 H17  SING N N 32 
I8E C18 H18C SING N N 33 
I8E C18 H18B SING N N 34 
I8E C18 H18A SING N N 35 
I8E C19 H19A SING N N 36 
I8E C19 H19C SING N N 37 
I8E C19 H19B SING N N 38 
I8E C2  H2B  SING N N 39 
I8E C2  H2A  SING N N 40 
I8E C20 H20C SING N N 41 
I8E C20 H20B SING N N 42 
I8E C20 H20A SING N N 43 
I8E C3  H3B  SING N N 44 
I8E C3  H3A  SING N N 45 
I8E C5  H5   SING N N 46 
I8E C8  H8   SING N N 47 
I8E C9  H9   SING N N 48 
I8E O21 H21  SING N N 49 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
I8E SMILES           ACDLabs              12.01 "CCCc1cc2OC(C)(C)C3CCC(C)=CC3c2c(O)c1"                                                                                         
I8E InChI            InChI                1.06  "InChI=1S/C19H26O2/c1-5-6-13-10-16(20)18-14-9-12(2)7-8-15(14)19(3,4)21-17(18)11-13/h9-11,14-15,20H,5-8H2,1-4H3/t14-,15-/m1/s1" 
I8E InChIKey         InChI                1.06  ZROLHBHDLIHEMS-HUUCEWRRSA-N                                                                                                    
I8E SMILES_CANONICAL CACTVS               3.385 "CCCc1cc(O)c2[C@@H]3C=C(C)CC[C@H]3C(C)(C)Oc2c1"                                                                                
I8E SMILES           CACTVS               3.385 "CCCc1cc(O)c2[CH]3C=C(C)CC[CH]3C(C)(C)Oc2c1"                                                                                   
I8E SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "CCCc1cc(c2c(c1)OC([C@H]3[C@H]2C=C(CC3)C)(C)C)O"                                                                               
I8E SMILES           "OpenEye OEToolkits" 2.0.7 "CCCc1cc(c2c(c1)OC(C3C2C=C(CC3)C)(C)C)O"                                                                                       
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
I8E "SYSTEMATIC NAME" ACDLabs              12.01 "(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-dibenzo[b,d]pyran-1-ol"             
I8E "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "(6~{a}~{R},10~{a}~{R})-6,6,9-trimethyl-3-propyl-6~{a},7,8,10~{a}-tetrahydrobenzo[c]chromen-1-ol" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
I8E "Create component" 2023-05-04 RCSB 
I8E "Initial release"  2023-08-23 RCSB 
# 
loop_
_pdbx_chem_comp_synonyms.ordinal 
_pdbx_chem_comp_synonyms.comp_id 
_pdbx_chem_comp_synonyms.name 
_pdbx_chem_comp_synonyms.provenance 
_pdbx_chem_comp_synonyms.type 
1 I8E "(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-dibenzo[b,d]pyran-1-ol" PDB ? 
2 I8E THCV                                                                                  PDB ? 
3 I8E THV                                                                                   PDB ? 
4 I8E O-4394                                                                                PDB ? 
5 I8E GWP42004                                                                              PDB ? 
# 
