有機概念図で見る環境ホルモン関連分子
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　本ページは，以下の資料の試験研究で用いられた化合物について紹介すると同時に，有機概念図計算の適用について試みるものです。

　なお本コンテンツは，日本環境化学会第12回討論会（2003/06/25-27，新潟市・朱鷺メッセ国際会議場）における以下の講演で発表した内容の一部です。
    講演番号55「有機概念図で見る環境ホルモン関連分子」　（県立新潟女子短期大学）本間善夫，金子祐子，津野あゆみ

    ※化合物検索と分子計算，有機概念図計算をしてくれた県立新潟女子短期大学2002年度入学生の金子祐子さんと津野あゆみさんに感謝します。

資料３の表2-2にあげられている化合物
※赤字は誤りと思われるものを修正した部分，CAS No.クリックで下窓にChime分子表示．
試験番号 化合物名 CAS No. ER_Binding
RBA%		 ER_Reporter
RA%		 化学式
2-001 beta-estradiol 50-28-2 126 81.7 C18H24O2
2-002 alpha-estradiol 57-91-0 80.1 1.27 C18H24O2
2-003 Estrone 53-16-7 44.2 1.39 C18H22O2
2-004 Estriol 50-27-1 33 24.7 C18H24O3
2-005 Ethynyl estradiol 57-63-6 142 81.7 C20H24O2
2-006 estradiol valerate 979-32-8 0.22 45.4 C23H32O3
2-009 beta-Estradiol 17-acetate 1743-60-8 1.84 81.7 C20H26O3
2-010 Estriol 3-methyl ether 1474-53-9 0.344 0.00397 C19H26O3
2-011 Estrone 3-methyl ether 1624-62-0 0.146 0.0206 C19H24O2
2-012 Estradiol dipropionate 113-38-2 0.00516 62.8 C24H32O4
2-013 Mestranol 72-33-3 9.09 0.126 C21H26O2
2-014 beta-Estradiol 17-cypionate 313-06-4 0.124 34 C26H36O3
2-015 beta-Estradiol 3-carboxymethyl ether 41164-36-7 0.00649 0.00785 C20H26O4
2-016 beta-Estradiol 17-hemisuccinate 7698-93-3 0.0267 17.8 C22H28O5
2-017 beta-Estradiol 17-enanthate 4956-37-0 0.225 62.8 C25H36O3
2-018 17alpha-Ethynylestradiol-3-cyclopentyl ether 152-43-2 1.01 0.37 C25H32O2
2-019 Estrone Acetate 901-93-9 1.32 14.6 C20H24O3
2-020 Estriol 3-carboxymethyl ether 69260-14-6 0.00765 0.00166 C20H26O5
2-021 beta-Estradiol 17-propionate 3758-34-7 0.62 81.7 C21H28O3
2-022 Estriol 3-benzyl ether 18650-87-8 0.0299 0.00257 C25H30O3
2-023 17-Epiestriol 1228-72-4 103 81.7 C18H24O3
2-024 Estriol 16,17-diacetate 805-26-5 1.26 81.7 C22H28O5
2-025 Estriol Triacetate 2284-32-4 0.00687 48 C24H30O6
2-026 16alpha-hydroxyestrone 566-76-7 6.5 2.12 C18H22O3
2-027 16-Ketoestradiol 566-75-6 30.6 81.7 C18H22O3
2-028 2-Hydroxyestradiol 362-05-0 81.3 0.0164 C18H24O3
2-029 4-Hydroxyestradiol 5976-61-4 7.88 0.249 C18H24O3
2-032 3-Deoxyestrone 53-45-2 0.116 0.00329 C18H22O
2-033 4-Hydroxyestrone 3131-23-5 1.31 0.00131 C18H22O3
2-034 2-Methoxyestrone 362-08-3 0.00601 0.0328 C19H24O3
2-035 6beta-Hydroxyestradiol-17beta 547-81-9 7.64 54.4 C18H24O3
2-036 6alpha-hydroxyestradiol 1229-24-9 59.7 0.395 C18H24O3
2-037 6-Ketoestradiol 571-92-6 66.4 81.7 C18H22O3
2-038 6-Dehydroestrone 2208-12-0 4.2 0.542 C18H20O2
2-039 6-Ketoestradiol 6-（O-carboxymethyl）oxime 35048-47-6 0.0803 0.0081 C20H25NO6
2-040 6-Ketoestrone 1476-34-2 7.77 0.166 C18H20O3
2-041 Equilin 474-86-2 28.9 10.9 C18H20O2
2-044 17-hydroxy-androstan-3-one 521-18-6 0.0218 0.00155 C19H30O2
2-045 Norethynodrel 68-23-5 0.282 0.543 C20H26O2
2-046 Norethrindrone 68-22-4 0.153 0.0165 C20H26O2
2-052 5alpha-Androstan-3beta-ol 1224-92-6 0.0553 0.000703 C19H32O
2-055 5alpha-Androstane-3beta,17beta-diol 571-20-0 1.28 0.636 C19H32O2
2-056 Dehydroepiandrosterone 53-43-0 0.018 0.0003 C19H28O2
2-064 Testosterone,19-nor 434-22-0 0.031 0.00302 C18H26O2
2-068 Estrone 3-hemisuccinate 58534-72-8 58.8 0.407 C23H28O5
2-074 Oxymetholone 434-07-1 0.0361 0.00015 C21H32O3
3-005 4-n-Amylphenol 14938-35-3 0.0032 0.000177 C11H16O
3-006 p-n-Hexylphenol 2446-69-7 0.00147 0.000176 C12H18O
3-007 4-Heptylphenol 1987-50-4 0.000853 0.0000831 C13H20O
3-009 4-dodecyl-phenol 104-43-8 0.238 0.00199 C18H30O
3-014 p-(tert-amyl) phenol 80-46-6 0.0173 0.000236 C11H16O
3-015 Nonylphenol （mixture）
※異性体の混合物（分子モデルは p-nonylphenol）		 25154-52-3 0.143 0.00518 C15H24O
3-017 4-tert-Octylphenol 140-66-9 0.124 0.0111 C14H22O
3-018 4-Cyclopentylphenol 1518-83-8 0.00251 0.0000851 C11H14O
3-019 4-Cyclohexylphenol 1131-60-8 0.0396 0.000542 C12H16O
3-020 4-（1-Adamantyl）phenol 29799-07-3 1.7 0.0439 C16H20O
3-022 4-Nonylphenol 84852-15-3 0.108 0.00507 C15H24O
3-043 Butylparaben 94-26-8 0.018 0.000687 C11H14O3
3-044 Hexyl p-hydroxybenzoate 1083-27-8 0.0068 0.000812 C13H18O3
3-045 n-Dodecyl 4-hydroxybenzoate 2664-60-0 0.00527 0.281 C19H30O3
3-046 2-Ethylhexyl 4-hydroxybenzoate 5153-25-3 0.0519 0.0035 C15H22O3
3-047 Propylparaben 94-13-3 0.0093 0.000389 C10H12O3
3-048 n-Amyl-4-hydroxybenzoate 6521-29-5 0.00568 0.000956 C12H16O3
3-049 Benzyl-4-hydroxybenzoate 94-18-8 0.00473 0.000592 C14H12O3
3-050 Isopropyl-4-hydroxybenzoate 4191-73-5 0.0453 0.00064 C10H12O3
3-051 4-Hydroxybenzoic Acid Isoamyl Ester 6521-30-8 0.0241 0.000802 C12H16O3
3-058 p-(pentyloxy)phenol 18979-53-8 0.000814 0.000105 C11H16O2
3-064 4-Cyclohexylresorcinol 2138-20-7 0.0147 0.000217 C12H16O2
3-079 4-Hexanoylresorcinol 3144-54-5 0.00438 0.000644 C12H16O3
3-083 4-Hydroxynonanophenone 14392-69-9 0.00151 0.000163 C15H22O2
3-162 Di-n-pentylphthalate 131-18-0 0.00165 0.000613 C18H26O4
3-178 Dibenzyl phthalate 523-31-9 0.0189 0.000312 C22H18O4
3-183 Butylbenzyl phthalate 85-68-7 0.00318 0.000199 C19H20O4
3-314 1,1-Bis(4-hydroxyphenyl)-iso-butane 1844-00-4 0.255 0.00183 C16H18O2
4-008 p-Phenylphenol 92-69-3 0.0173 0.000229 C12H10O
4-011 4,4-Dihydroxydiphenyl 92-88-6 0.0883 0.00028 C12H10O2
4-014 4-Hydroxy-4'-chlorobiphenyl 28034-99-3 0.0545 0.000582 C12H9ClO
4-015 4-（4-bromophenyl）phenol 29558-77-8 0.0943 0.000648 C12H9BrO
4-016 4'-Methoxy-biphenyl-4-ol 16881-71-3 0.0365 0.00053 C13H12O2
4-018 4'-Hydroxy-4-biphenylcarbonitrile 19812-93-2 0.00144 0.000246 C13H9NO
4-023 4-(Phenylmethyl)-phenol 101-53-1 0.0223 0.0002 C13H12O
4-024 4,4'-Dihydroxydiphenylmethane 620-92-8 0.0719 0.00063 C13H12O2
4-025 4,4'-Ethylidenebisphenol 2081-08-5 0.0715 0.00077 C14H14O2
4-026 4-alpha-Cumylphenol 599-64-4 0.107 0.00051 C15H16O
4-027 Bisphenol A 80-05-7 0.195 0.00278 C15H16O2
4-028 2,2-bis-（4-Hydroxyphenyl）-butane 77-40-7 0.593 0.00388 C16H18O2
4-029 2,2-Bis(4-hydroxyphenyl)-4-methyl-n-pentane 6807-17-6 2.79 0.041 C18H22O2
4-030 4,4'-（1-Phenylethylidene）bisphenol 1571-75-1 0.0803 0.00018 C20H18O2
4-031 tris(Hydroxyphenyl)ethane 27955-94-8 0.0407 0.00035 C20H18O3
4-032 2-[Bis(4-hydroxyphenyl)methyl]benzylalcohol= Phenolphthalol 81-92-5 0.119 0.00059 C20H18O3
4-033 4,4'-（Hexafluoroisopropylidene）diphenol 1478-61-1 0.774 0.0102 C15H10F6O2
4-034 4,4'-Cyclohexylidenebisphenol 843-55-0 0.212 0.00277 C18H20O2
4-044 4,4'-Sulfonyldiphenol 80-09-1 0.0055 0.00025 C12H10O4S
4-047 m-Cresol purple, sodium salt 62625-31-4 0.00383 0.000154 C21H17NaO5S
4-050 2,2-Bis-(3,5-dimethyl-4-hydroxyphenyl)-propane 5613-46-7 0.0195 0.000201 C19H24O2
4-052 2,2-Bis(4-hydroxy-3-methylphenyl)propane 79-97-0 0.129 0.00189 C17H20O2
4-065 o,p'-DDD 53-19-0 0.00571 0.000186 C14H10Cl4
4-078 4,4'-Ethylenedi-m-toluidine 22856-62-8 0.00189 0.000237 C16H20N2
4-081 Hexestrol 84-16-2 37.6 29.2 C18H22O2
4-082 Dehydrostilbestrol 84-17-3 20.6 8.97 C18H18O2
4-087 Benzyl 2,4-dihydroxyphenylketone 3669-41-8 0.00213 0.000122 C14H12O3
4-088 Benzyl 4-hydroxyphenylketone 2491-32-9 0.00386 0.000485 C14H12O2
4-089 Hexestrol dipropionate 4825-53-0 0.269 81.7 C24H30O4
4-091 Diethylstilbestrol 56-53-1 88.9 40.8 C18H20O2
4-094 4-Amino-4'-hydroxystilbene 836-44-2 0.00111 0.000565 C14H13NO
4-095 Piceatannol 10083-24-6 0.00914 0.000311 C14H12O4
4-097 Resveratrol 501-36-0 0.00314 0.000677 C14H12O3
4-100 Diethylstilbestrol dipropionate 130-80-3 9.82 81.7 C24H28O4
4-101 Triphenylethylene 58-72-0 0.0736 0.000556 C20H16
4-103 4-Hydroxybenzophenone 1137-42-4 0.0108 0.000314 C13H10O2
4-105 3-Hydroxybenzophenone 13020-57-0 0.013 0.000318 C13H10O2
4-106 4,4'-Dihydroxybenzophenone 611-99-4 0.017 0.000495 C13H10O3
4-107 2,4-Dihydroxybenzophenone 131-56-6 0.0139 0.000338 C13H10O3
4-108 2,4,4'-Trihydroxybenzophenone 1470-79-7 0.0738 0.00218 C13H10O4
4-112 2,2',4,4'-Tetrahydroxybenzophenone 131-55-5 0.0925 0.00249 C13H10O5
4-113 4-Chloro-4'-hydroxybenzophenone 42019-78-3 0.00812 0.000463 C13H9ClO2
4-114 4-Fluoro-4'-hydroxybenzophenone 25913-05-7 0.00314 0.000417 C13H9FO2
4-117 4,4'-Dibromobenzophenone 3988-03-2 0.00821 0.000308 C13H8Br2O
4-118 4-Phenoxyphenol 831-82-3 0.0579 0.0000826 C12H10O2
4-119 Hydroquinone monobenzylether 103-16-2 0.00104 0.000229 C13H12O2
4-120 4,4'-Oxydiphenol 1965-09-9 0.17 0.000342 C12H10O3
4-132 4-Hydroxychalcone 20426-12-4 0.00123 0.000591 C15H12O2
4-137 4-Hydroxyazobenzene 1689-82-3 0.0747 0.000754 C12H10N2O
4-139 4,4'-(1,3-Adamantanediyl) diphenol 37677-93-3 0.383 0.00509 C22H24O2
4-143 Phloretin 60-82-2 0.0154 0.000165 C15H14O5
4-144 3,3,3',3'-Tetramethyl-1,1'-spirobisindane-5,5',6,6'-tetrol 77-08-7 0.0999 0.000259 C21H24O4
4-145 Isoliquirtigenin 961-29-5 0.0528 0.00315 C15H12O4
4-147 4,4'-Thiobis-phenol 2664-63-3 0.243 0.00382 C12H10O2S
4-163 Sudan orange G 2051-85-6 0.00415 0.000522 C12H10N2O2
4-184 a,a'-Diethyl-4,4'-dihydroxystilbene= cis-Diethylstilbestrol 6898-97-1 65.9 20.6 C18H20O2
4-217 trans-4-Hydroxystilbene 6554-98-9 0.0133 0.000717 C14H12O
4-222 Bromotriphenylethylene 1607-57-4 2.71 0.00815 C20H15Br
4-241 4,4'-(Hexafluoroisopropylidene)dianiline 1095-78-9 0.0571 0.000257 C15H12F6N2
4-259 trans-1,2-Bis(4-fluorobenzoyl)ethylene 25650-13-9 0.0222 0.000124 C16H10F2O2
5-001 Biochanin A 491-80-5 0.00126 0.000758 C16H12O5
5-002 Daidzein 486-66-8 0.18 0.0054 C15H10O4
5-003 2-Carbethoxy-5,7-dihydroxy-4'-methoxyisoflavone 15485-76-4 0.0429 0.00042 C19H16O7
5-005 3',4',7-Trihydroxyisoflavone 485-63-2 0.0378 0.000605 C15H10O5
5-006 Kaempferol 520-18-3 0.029 0.000673 C15H10O6
5-007 Naringenin 480-41-1 0.00533 0.000552 C15H12O5
5-008 Luteolin 491-70-3 0.00336 0.000362 C15H10O6
5-011 Morin 480-16-0 0.0011 0.000196 C15H10O7
5-012 apigenin 520-36-5 0.0179 0.00143 C15H10O5
5-013 (+/-)-Naringenin
※ラセミ体のため分子モデル略（一方は5-007）		 93602-28-9
 0.00155 0.000518 C15H12O5
5-014 6-Hydroxyflavanone 4250-77-5 0.0183 0.000322 C15H12O3
5-016 Benz(a)anthracene 56-55-3 0.0518 0.00178 C18H12
5-022 6-Bromo-2-naphthol 15231-91-1 0.00216 0.000173 C10H7BrO
5-028 p-Naphtholbenzein 145-50-6 0.245 0.00177 C27H18O2
5-029 2-Hydroxy-9-fluorenone 6949-73-1 0.00195 0.000191 C13H8O2
5-031 6-Benzoyl-2-naphthol 52222-87-4 0.0184 0.00239 C17H12O2
5-032 2-hydroxyfluorene 2443-58-5 0.00061 0.000323 C13H10O
5-040 6-Hydroxy-2-naphthyl disulfide 6088-51-3 0.0669 0.000675 C20H14O2S2
5-054 Alternariol 641-38-3 0.0101 0.000245 C14H10O5
5-067 6-Hydroxyflavone 6665-83-4 0.00482 0.00037 C15H10O3
5-093 alpha-Naphtholbenzein 6948-88-5 0.356 0.00119 C27H20O3
5-095 Formononetin 485-72-3 0.0265 0.00238 C16H12O4
5-098 2,3-Diphenyl-1-indenone 1801-42-9 0.0784 0.000332 C21H14O
5-099 alpha-Naphtholphthalein 596-01-0 0.0389 0.0021 C28H18O4
6-001 Zearalenone 17924-92-4 2.83 1.27 C18H22O5
6-002 beta-Zearalanol 42422-68-4 17.6 0.954 C18H26O5
6-003 alpha-Zearalenol 36455-72-8 52.7 81.7 C18H24O5
6-004 beta-Zearalenol 71030-11-0 1.68 0.035 C18H24O5
6-005 Zearalanone 5975-78-0 3.22 2.58 C18H22O5
6-006 Coumestrol 479-13-0 0.264 0.0408 C15H8O5
6-007 Genistein 446-72-0 0.12 0.0334 C15H10O5
6-013 3-Phenylumbelliferone 6468-96-8 0.0229 0.000789 C15H10O3
6-019 Kepone 143-50-0 0.0155 0.000106 C10Cl10O
6-043 3-(2-Benzothiazolyl)umbelliferone 58851-99-3 0.00631 0.0007 C16H9NO3S

試験番号の分類
試験番号 種別
2 ステロイド
3 ベンゼン単環
4 非縮合多環
5 縮合多環
6 その他


図１　上記化合物の有機概念図上の分布
参考：他の環境ホルモン関連化合物の有機概念図（図２）

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