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Brucea mollis

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Table of Contents

Details
Description
Synonyms
Common Names
Subtypes (subspecies, varieties, subvarieties, forms)
Germination/Propagation
Distribution
Links to other databases
Genome
Scientific Literature
Phytochemical Profile
Biological Material
Contributors
Collections

Details Top

Internal ID UUID64400de379782142082237
Scientific name Brucea mollis
Authority Wall. ex Kurz
First published in J. Asiat. Soc. Bengal, Pt. 2, Nat. Hist. 42: 64 (1873)

Description Top

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Synonyms Top

Scientific name Authority First published in
Lussa mollis Kuntze Revis. Gen. Pl. 1: 104 (1891)
Brucea acuminata H.L.Li J. Arnold Arbor. 24: 445 (1943)
Brucea luzoniensis S.Vidal Sin. Gen. Pl. Leños. Filip. , Atlas: xix (1883)
Brucea macrobotrys Merr. Philipp. J. Sci., C 10: 19 (1915)
Brucea membranacea Merr. Philipp. J. Sci. 1(Suppl.): 70 (1906)
Brucea stendphylla Merr. Philipp. J. Sci., C 12: 271 (1917)

Common names Top

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Language Common/alternative name
Chinese 柔毛鸦胆子
Chinese 鸦胆子
Chinese 大果鸦胆子
Chinese 毛鸦胆子

Subspecies (abbr. subsp./ssp.) Top

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Varieties (abbr. var.) Top

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Subvarieties (abbr. subvar.) Top

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Forms (abbr. f.) Top

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Germination/Propagation Top

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Distribution (via POWO/KEW) Top

No distribution data was extracted from POWO/KEW yet. We are constantly monitoring for new data.

Links to other databases Top

Suggest others/fix!
Database ID/link to page
World Flora Online wfo-0000572711
Tropicos 50126883
KEW urn:lsid:ipni.org:names:60469132-2
The Plant List kew-2683976
Open Tree Of Life 708239
NCBI Taxonomy 43723
IPNI 813615-1
GBIF 5555195
EOL 2905835
CMAUP NPO15436

Genomes (via NCBI) Top

No reference genome is available on NCBI yet. We are constantly monitoring for new data.

Scientific Literature Top

Below are displayed the latest 15 articles published in PMC (PubMed Central®) and other sources (DOI number only)!
If you wish to see all the related articles click here.
Title Authors Publication Released IDs
Canthin-6-Ones: Potential Drugs for Chronic Inflammatory Diseases by Targeting Multiple Inflammatory Mediators Zhang Z, Wang A, Wang Y, Sun W, Zhou X, Xu Q, Mao L, Zhang J Molecules 11-Apr-2023
PMCID:PMC10141368
doi:10.3390/molecules28083381
PMID:37110614
Natural products targeting glycolysis in cancer Zhao Y, Chard Dunmall LS, Cheng Z, Wang Y, Si L Front Pharmacol 01-Nov-2022
PMCID:PMC9663463
doi:10.3389/fphar.2022.1036502
PMID:36386122
Geosmithia Species Associated With Bark Beetles From China, With the Description of Nine New Species Zhang X, Li Y, Si H, Zhao G, Kolařík M, Hulcr J, Jiang X, Dai M, Chang R Front Microbiol 14-Mar-2022
PMCID:PMC8964297
doi:10.3389/fmicb.2022.820402
PMID:35369427
In Vitro Production and Exudation of 20-Hydroxymaytenin from Gymnosporia heterophylla (Eckl. and Zeyh.) Loes. Cell Culture Pitakbut T, Spiteller M, Kayser O Plants (Basel) 21-Jul-2021
PMCID:PMC8398937
doi:10.3390/plants10081493
PMID:34451538
Biological Activity of Naturally Derived Naphthyridines Chabowska G, Barg E, Wójcicka A Molecules 16-Jul-2021
PMCID:PMC8306249
doi:10.3390/molecules26144324
PMID:34299599
Nephrotoxicity and Chinese Herbal Medicine Yang B, Xie Y, Guo M, Rosner MH, Yang H, Ronco C Clin J Am Soc Nephrol 03-Apr-2018
PMCID:PMC6218812
doi:10.2215/CJN.11571017
PMID:29615394
Bruceolline J: 2-hy­droxy-3,3-dimethyl-2,3-di­hydro­cyclo­penta­[b]indol-1(4H)-one Lopchuk JM, Gribble GW, Millikan SP, Jasinski JP Acta Crystallogr Sect E Struct Rep Online 31-Jul-2013
PMCID:PMC3793830
doi:10.1107/S1600536813020527
PMID:24109417
Medicinal plants from swidden fallows and sacred forest of the Karen and the Lawa in Thailand Junsongduang A, Balslev H, Inta A, Jampeetong A, Wangpakapattanawong P J Ethnobiol Ethnomed 24-Jun-2013
PMCID:PMC3702467
doi:10.1186/1746-4269-9-44
PMID:23800255
Bruceolline D: 3,3-dimethyl-1H,4H-cyclo­penta­[b]indol-2(3H)-one Lopchuk JM, Gribble GW, Jasinski JP Acta Crystallogr Sect E Struct Rep Online 08-Jun-2013
PMCID:PMC3772476
doi:10.1107/S1600536813014955
PMID:24046619
Cytotoxic Compounds from Brucea mollis Tung MH, Đuc HV, Huong TT, Duong NT, Phuong DT, Thao DT, Tai BH, Kim YH, Bach TT, Cuong NM Sci Pharm 31-Dec-2012
PMCID:PMC3791942
doi:10.3797/scipharm.1206-02
PMID:24106661
3,3-Dimethyl-1,2,3,4-tetra­hydro­cyclo­penta­[b]indole-1,2-dione (bruceolline E) Jordon JA, Badenock JC, Gribble GW, Jasinski JP, Golen JA Acta Crystallogr Sect E Struct Rep Online 11-Jan-2012
PMCID:PMC3275045
doi:10.1107/S1600536812000517
PMID:22346990
Indole alkaloids and quassinoids from the stems of Brucea mollis. Chen H, Bai J, Fang ZF, Yu SS, Ma SG, Xu S, Li Y, Qu J, Ren JH, Li L, Si YK, Chen XG J Nat Prod 28-Nov-2011
doi:10.1021/NP200712Y
PMID:22070654
Alkaloids and quassinoids of Brucea mollis var. tonkinensis Yishan Ouyang, Katsuyoshi Mitsunaga, Kazuo Koike, Taichi Ohmoto Elsevier BV 30-Apr-2003
doi:10.1016/0031-9422(95)00039-A
Indole alkaloids from Brucea mollis var. Tonkinensis Yishan Ouyang Kazuo Koike, Taichi Ohmoto Elsevier BV 25-Jul-2002
doi:10.1016/0031-9422(94)85103-4
Canthin-6-one alkaloids from Brucea mollis var. tonkinensis. Ouyang Y, Koike K, Ohmoto T Phytochemistry 01-Aug-1994
doi:10.1016/S0031-9422(00)89758-7
PMID:7765437

Phytochemical Profile Top

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Below are displayed the proven (via scientific papers) natural compounds!
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Name PubChem ID Canonical SMILES MW Found in Proof
> Alkaloids and derivatives / Harmala alkaloids
(4aS,9aR)-1-ethyl-9,9a-dihydro-4aH-pyrido[3,4-b]indole 162925977 Click to see CCC1=NC=CC2C1NC3=CC=CC=C23 198.26 unknown https://doi.org/10.1016/0031-9422(95)00039-A
[(4aS,9aR)-9,9a-dihydro-4aH-pyrido[3,4-b]indol-1-yl]methanol 162990083 Click to see C1=CC=C2C(=C1)C3C=CN=C(C3N2)CO 200.24 unknown https://doi.org/10.1016/0031-9422(95)00039-A
1-ethyl-9,9a-dihydro-4aH-pyrido[3,4-b]indole 162925976 Click to see CCC1=NC=CC2C1NC3=CC=CC=C23 198.26 unknown https://doi.org/10.1016/0031-9422(95)00039-A
1-ethyl-9H-pyrido[3,4-b]indole 5324325 Click to see CCC1=NC=CC2=C1NC3=CC=CC=C23 196.25 unknown https://doi.org/10.1016/0031-9422(95)00039-A
2-(9,9a-dihydro-4aH-pyrido[3,4-b]indol-1-yl)ethanol 162927167 Click to see C1=CC=C2C(=C1)C3C=CN=C(C3N2)CCO 214.26 unknown https://doi.org/10.1016/0031-9422(95)00039-A
2-[(4aS,9aR)-9,9a-dihydro-4aH-pyrido[3,4-b]indol-1-yl]ethanol 162927168 Click to see C1=CC=C2C(=C1)C3C=CN=C(C3N2)CCO 214.26 unknown https://doi.org/10.1016/0031-9422(95)00039-A
9,9a-dihydro-4aH-pyrido[3,4-b]indol-1-ylmethanol 162990082 Click to see C1=CC=C2C(=C1)C3C=CN=C(C3N2)CO 200.24 unknown https://doi.org/10.1016/0031-9422(95)00039-A
> Alkaloids and derivatives / Indolonaphthyridine alkaloids
11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one 162969859 Click to see C1=CC2=C(C3=C4N2C(=O)C=CC4=NC=C3)C(=C1)OC5C(C(C(C(O5)CO)O)O)O 398.40 unknown https://doi.org/10.1016/0031-9422(95)00039-A
11-[3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one 162969858 Click to see C1=CC2=C(C3=C4N2C(=O)C=CC4=NC=C3)C(=C1)OC5C(C(C(C(O5)CO)O)O)O 398.40 unknown https://doi.org/10.1016/0031-9422(95)00039-A
11-[3,4,5-Trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one 78173562 Click to see C1=CC2=C(C3=C4N2C(=O)C=CC4=NC=C3)C(=C1)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O 560.50 unknown https://doi.org/10.1016/S0031-9422(00)89758-7
11-hydroxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one 5281405 Click to see C1=CC2=C(C3=C4N2C(=O)C=CC4=NC=C3)C(=C1)O 236.22 unknown https://doi.org/10.1016/0031-9422(95)00039-A
11-Hydroxycanthin-6-one 337601 Click to see C1=CC(=O)C2=C3C=CNC4=C3N(C2=C1)C(=O)C=C4 236.22 unknown https://doi.org/10.1016/0031-9422(95)00039-A
12-Hydroxy-8,11-dimethoxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one 163028349 Click to see COC1=CN=C2C=CC(=O)N3C2=C1C4=C3C=CC(=C4OC)O 296.28 unknown https://doi.org/10.1016/0031-9422(95)00039-A
3-[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one 101672256 Click to see C1=CC=C2C(=C1)C3=C4N2C(=O)C(=CC4=NC=C3)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O 560.50 unknown https://doi.org/10.1016/S0031-9422(00)89758-7
3-[3,4,5-Trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one 78173563 Click to see C1=CC=C2C(=C1)C3=C4N2C(=O)C(=CC4=NC=C3)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O 560.50 unknown https://doi.org/10.1016/S0031-9422(00)89758-7
8-Hydroxy-11-methoxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one 86132504 Click to see COC1=CC=CC2=C1C3=C4N2C(=O)C=CC4=NC=C3O 266.25 unknown https://doi.org/10.1016/0031-9422(95)00039-A
Bruceolline A 190939 Click to see C1=CC2=C(C3=C4N2C(=O)C=CC4=NC=C3)C(=C1)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O 560.50 unknown https://doi.org/10.1016/S0031-9422(00)89758-7
Bruceolline B 190940 Click to see C1=CC=C2C(=C1)C3=C4N2C(=O)C(=CC4=NC=C3)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O 560.50 unknown https://doi.org/10.1016/S0031-9422(00)89758-7
Canthin-6-one 97176 Click to see C1=CC=C2C(=C1)C3=C4N2C(=O)C=CC4=NC=C3 220.23 unknown https://doi.org/10.1016/S0031-9422(00)89758-7
> Lignans, neolignans and related compounds / Furanoid lignans
Epipinoresinol 637584 Click to see COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O 358.40 unknown via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Monoterpenoids / Aromatic monoterpenoids
3-Isopropyl-4-acetoxy-6-methylbenzene-1,2-diol 14287134 Click to see CC1=CC(=C(C(=C1O)O)C(C)C)OC(=O)C 224.25 unknown via CMAUP database
Thymol 6989 Click to see CC1=CC(=C(C=C1)C(C)C)O 150.22 unknown via CMAUP database
Thymol acetate 68252 Click to see CC1=CC(=C(C=C1)C(C)C)OC(=O)C 192.25 unknown via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Sesquiterpenoids
Caryophyllene 5281515 Click to see CC1=CCCC(=C)C2CC(C2CC1)(C)C 204.35 unknown via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Terpene lactones / Quassinoids
2,3,12,15,16-Pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-4,11-dione 432922 Click to see CC1=CC(=O)C(C2(C1CC3C45C2C(C(C(C4(C(C(=O)O3)O)O)(OC5)C)O)O)C)O 410.40 unknown https://doi.org/10.1016/0031-9422(95)00039-A
Brucein B 280689 Click to see CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C)(OC5)C(=O)OC)O)O)C)O 480.50 unknown https://doi.org/10.1016/0031-9422(95)00039-A
Brucein D 441788 Click to see CC1=CC(=O)C(C2(C1CC3C45C2C(C(C(C4(C(C(=O)O3)O)O)(OC5)C)O)O)C)O 410.40 unknown https://doi.org/10.1016/0031-9422(95)00039-A
Bruceine D 122784 Click to see CC1=CC(=O)C(C2(C1CC3C45C2C(C(C(C4(C(C(=O)O3)O)O)(OC5)C)O)O)C)O 410.40 unknown https://doi.org/10.1021/NP200712Y
Bruceoside B 72953 Click to see CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C)(OC5)C(=O)OC)O)O)C)OC6C(C(C(C(O6)CO)O)O)O 682.70 unknown https://doi.org/10.1016/0031-9422(95)00039-A
Brusatol 73432 Click to see CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C)(OC5)C(=O)OC)O)O)C)O 520.50 unknown https://doi.org/10.1016/0031-9422(95)00039-A
methyl (1R,2R,6R,8S,13S,14S,17S)-10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate 137704670 Click to see CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C)(OC5)C(=O)OC)O)O)C)O 520.50 unknown https://doi.org/10.1016/0031-9422(95)00039-A
methyl (1R,3R,8R,13S,14R,15R,16S,17S)-3-acetyloxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate 118701103 Click to see CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C)(OC5)C(=O)OC)O)O)C)O 480.50 unknown https://doi.org/10.1016/0031-9422(95)00039-A
Rel-Yadanziolide V 56833964 Click to see CC1=CC(=O)OC1C2(CC3C4(C2C(C(C(C4C(C(=O)O3)O)CO)O)O)C)C 382.40 unknown https://doi.org/10.1021/NP200712Y
Soulameanone 330352 Click to see CC1=CC(=O)C(C2(C1CC3C4(C2C(C(C(C4C(C(=O)O3)O)(C)O)O)O)C)C)O 396.40 unknown https://doi.org/10.1016/0031-9422(95)00039-A
Yadanziolide B 11744055 Click to see CC1=CC(=O)C(C2(C1C(C3C45C2C(C(C(C4(C(C(=O)O3)O)O)(OC5)CO)O)O)O)C)O 442.40 unknown https://doi.org/10.1021/NP200712Y
Yadanziolide T 56833962 Click to see CC1=CC(=O)C(C2(C1CC3C4(C2C(C(C(C4C(C(=O)O3)O)CO)O)O)C)C)O 396.40 unknown https://doi.org/10.1021/NP200712Y
Yadanziolide U 56833963 Click to see CC1=CC(=O)C(C2(C1CC3C4(C2C(C(C(C4C(C(=O)O3)O)COC5C(C(C(C(O5)CO)O)O)O)O)O)C)C)O 558.60 unknown https://doi.org/10.1021/NP200712Y
> Nucleosides, nucleotides, and analogues / Nucleoside and nucleotide analogues / 1-pyranosylindoles
(2R,3R,4S,5S,6R)-2-[3-[(2R)-2,3-dihydroxy-3-methylbutyl]indol-1-yl]-6-(hydroxymethyl)oxane-3,4,5-triol 38355092 Click to see CC(C)(C(CC1=CN(C2=CC=CC=C21)C3C(C(C(C(O3)CO)O)O)O)O)O 381.40 unknown https://doi.org/10.1016/0031-9422(94)85103-4
2-[3-(2,3-Dihydroxy-3-methylbutyl)indol-1-yl]-6-(hydroxymethyl)oxane-3,4,5-triol 75061284 Click to see CC(C)(C(CC1=CN(C2=CC=CC=C21)C3C(C(C(C(O3)CO)O)O)O)O)O 381.40 unknown https://doi.org/10.1016/0031-9422(94)85103-4
Bruceolline F 38355088 Click to see CC(C)(C(CC1=CN(C2=CC=CC=C21)C3C(C(C(C(O3)CO)O)O)O)O)O 381.40 unknown https://doi.org/10.1016/0031-9422(94)85103-4
https://doi.org/10.1021/NP200712Y
Bruceolline M 56833861 Click to see CC(C)(C(=O)CC1=CN(C2=CC=CC=C21)C3C(C(C(C(O3)CO)O)O)O)O 379.40 unknown https://doi.org/10.1021/NP200712Y
Bruceolline N 56833961 Click to see CC(C)(C(CC1(C2=CC=CC=C2N(C1=O)C3C(C(C(C(O3)CO)O)O)O)O)O)O 413.40 unknown https://doi.org/10.1021/NP200712Y
> Organic oxygen compounds / Organooxygen compounds / Carbohydrates and carbohydrate conjugates / Glycosyl compounds / O-glycosyl compounds
Bruceolline K 56833859 Click to see CC1(C(C(=O)C2=C1NC3=CC=CC=C32)OC4C(C(C(C(O4)CO)O)O)O)C 377.40 unknown https://doi.org/10.1021/NP200712Y
> Organic oxygen compounds / Organooxygen compounds / Carbonyl compounds / Benzoquinones / P-benzoquinones
2-Isopropyl-3-acetoxy-5-methyl-2,5-cyclohexadiene-1,4-dione 14287135 Click to see CC1=CC(=O)C(=C(C1=O)OC(=O)C)C(C)C 222.24 unknown via CMAUP database
Thymoquinone 10281 Click to see CC1=CC(=O)C(=CC1=O)C(C)C 164.20 unknown via CMAUP database
> Organoheterocyclic compounds / Indoles and derivatives / Hydroxyindoles
Bruceolline H 56833856 Click to see CC1(C2=C(C3=C(N2)C=C(C=C3)O)C(=O)C1=O)C 229.23 unknown https://doi.org/10.1021/NP200712Y
Bruceolline I 56833857 Click to see CC1(C(C(=O)C2=C1NC3=C2C=CC(=C3)O)O)C 231.25 unknown https://doi.org/10.1021/NP200712Y
> Organoheterocyclic compounds / Indoles and derivatives / Indoles
Bruceolline E 56945466 Click to see CC1(C2=C(C3=CC=CC=C3N2)C(=O)C1=O)C 213.23 unknown https://doi.org/10.1016/0031-9422(94)85103-4
https://doi.org/10.1021/NP200712Y
Bruceolline J 56833858 Click to see CC1(C(C(=O)C2=C1NC3=CC=CC=C32)O)C 215.25 unknown https://doi.org/10.1021/NP200712Y
Bruceolline L 56833860 Click to see CC(C)C(C(=O)C1=CNC2=CC=CC=C21)O 217.26 unknown https://doi.org/10.1021/NP200712Y
> Organoheterocyclic compounds / Indoles and derivatives / Indoles / 3-alkylindoles
Bruceolline D 12387437 Click to see CC1(C(=O)CC2=C1NC3=CC=CC=C23)C 199.25 unknown https://doi.org/10.1016/0031-9422(94)85103-4
> Organoheterocyclic compounds / Indoles and derivatives / Pyridoindoles / Beta carbolines
9H-Pyrido[3,4-B]indole 64961 Click to see C1=CC=C2C(=C1)C3=C(N2)C=NC=C3 168.19 unknown https://doi.org/10.1016/0031-9422(95)00039-A
> Organoheterocyclic compounds / Lactones / Delta valerolactones
(1S,2S,6S,7S,9R,11R)-12-[(2S)-2-(furan-3-yl)-2-hydroxyethyl]-7-hydroxy-11-methyl-8,14-dioxatetracyclo[7.6.0.01,6.02,12]pentadecan-13-one 163195645 Click to see CC1CC2C34COC(=O)C1(C3CCCC4C(O2)O)CC(C5=COC=C5)O 362.40 unknown https://doi.org/10.1016/0031-9422(95)00039-A
> Organoheterocyclic compounds / Pyridines and derivatives / Bipyridines and oligopyridines
7-(1-Methyl-2-oxopropyl)streptonigrin 135437981 Click to see CC1=C(C(=C(N=C1C(=O)O)C2=NC3=C(C=C2)C(=O)C(=C(C3=O)NC(C)C(=O)C)OC)N)C4=C(C(=C(C=C4)OC)OC)O 576.60 unknown https://doi.org/10.1016/0031-9422(95)00039-A

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