Calanolide (BioDeep_00000007198)

Secondary id: BioDeep_00000176942, BioDeep_00001868580, BioDeep_00001892601

PANOMIX_OTCML-2023

代谢物信息卡片

Calanolide A

化学式: C22H26O5 (370.17801460000004)
中文名称: (+)-胡桐素A
谱图信息: 最多检出来源 Mus musculus(blood) 2.94%

分子结构信息

SMILES: CCCC1=CC(=O)OC2=C1C3=C(C=CC(O3)(C)C)C4=C2C(C(C(O4)C)C)O
InChI: InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3

描述信息

D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D044966 - Anti-Retroviral Agents

同义名列表

2 个代谢物同义名

Calanolide A; Calanolide

数据库引用编号

15 个数据库交叉引用编号

ChEBI: CHEBI:65552
KEGG: C09147
PubChem: 64972
PubChem: 1201
Metlin: METLIN67465
DrugBank: DB04886
ChEMBL: CHEMBL270362
ChEMBL: CHEMBL267447
KNApSAcK: C00019806
CAS: 142632-32-4
PMhub: MS000020491
PubChem: 11339
KNApSAcK: C00002454
3DMET: B02718
NIKKAJI: J500.414D

分类词条

香豆素

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

10 个相关的物种来源信息

999558 Calophyllum lanigerum: 10.1021/NP0203640
280748 Calophyllum brasiliense:
280748 Calophyllum brasiliense:
999558 Calophyllum lanigerum:
667334 Calophyllum teysmannii: 10.1016/S0960-894X(01)80543-6
999558 Calophyllum lanigerum: 10.1021/NP0203640
280748 Calophyllum brasiliense:
280748 Calophyllum brasiliense:
999558 Calophyllum lanigerum:
667334 Calophyllum teysmannii: 10.1016/S0960-894X(01)80543-6

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

文献列表

J C Gomez-Verjan, E Estrella-Parra, E R Vazquez-Martinez, I Gonzalez-Sanchez, G Guerrero-Magos, D Mendoza-Villanueva, L Isus, A Alfaro, M Cerbón-Cervantes, P Aloy, R Reyes-Chilpa. Risk assessment of Soulatrolide and Mammea (A/BA+A/BB) coumarins from Calophyllum brasiliense by a toxicogenomic and toxicological approach. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2016 May; 91(?):117-29. doi: 10.1016/j.fct.2016.03.010. [PMID: 26995226]
Irena Kostova. Coumarins as inhibitors of HIV reverse transcriptase. Current HIV research. 2006 Jul; 4(3):347-63. doi: 10.2174/157016206777709393. [PMID: 16842086]
Maira Huerta-Reyes, Maria Del Carmen Basualdo, Fumiko Abe, Manuel Jimenez-Estrada, Carmen Soler, Ricardo Reyes-Chilpa. HIV-1 inhibitory compounds from Calophyllum brasiliense leaves. Biological & pharmaceutical bulletin. 2004 Sep; 27(9):1471-5. doi: 10.1248/bpb.27.1471. [PMID: 15340243]
Quyet Chien Nguyen, Van Hung Nguyen, Bernard D Santarsiero, Andrew D Mesecar, Manh Cuon Nguyen, D Doel Soejarto, John M Pezzuto, Harry H S Fong, Ghee T Tan. New 3-O-acyl betulinic acids from Strychnos vanprukii Craib. Journal of natural products. 2004 Jun; 67(6):994-8. doi: 10.1021/np030469i. [PMID: 15217281]
Paul Cos, Louis Maes, Dirk Vanden Berghe, Nina Hermans, Luc Pieters, Arnold Vlietinck. Plant substances as anti-HIV agents selected according to their putative mechanism of action. Journal of natural products. 2004 Feb; 67(2):284-93. doi: 10.1021/np034016p. [PMID: 14987070]
Chihiro Ito, Masataka Itoigawa, Yoshitaka Mishina, Valdir Cechinel Filho, Fumio Enjo, Harukuni Tokuda, Hoyoku Nishino, Hiroshi Furukawa. Chemical constituents of Calophyllum brasiliense. 2. Structure of three new coumarins and cancer chemopreventive activity of 4-substituted coumarins. Journal of natural products. 2003 Mar; 66(3):368-71. doi: 10.1021/np0203640. [PMID: 12662094]
David A Eiznhamer, Terri Creagh, Jon L Ruckle, Dwain T Tolbert, Jeremy Giltner, Bipul Dutta, Michael T Flavin, Tuah Jenta, Ze-Qi Xu. Safety and pharmacokinetic profile of multiple escalating doses of (+)-calanolide A, a naturally occurring nonnucleoside reverse transcriptase inhibitor, in healthy HIV-negative volunteers. HIV clinical trials. 2002 Nov; 3(6):435-50. doi: 10.1310/9gde-f2r1-w2rl-e9fj. [PMID: 12501127]
H R W Dharmaratne, G T Tan, G P K Marasinghe, J M Pezzuto. Inhibition of HIV-1 reverse transcriptase and HIV-1 replication by Calophyllum coumarins and xanthones. Planta medica. 2002 Jan; 68(1):86-7. doi: 10.1055/s-2002-20058. [PMID: 11842340]
T Creagh, J L Ruckle, D T Tolbert, J Giltner, D A Eiznhamer, B Dutta, M T Flavin, Z Q Xu. Safety and pharmacokinetics of single doses of (+)-calanolide a, a novel, naturally occurring nonnucleoside reverse transcriptase inhibitor, in healthy, human immunodeficiency virus-negative human subjects. Antimicrobial agents and chemotherapy. 2001 May; 45(5):1379-86. doi: 10.1128/aac.45.5.1379-1386.2001. [PMID: 11302799]
Z Q Xu, K J Norris, D S Weinberg, J Kardatzke, P Wertz, P Frank, M T Flavin. Quantification of (+)-calanolide A, a novel and naturally occurring anti-HIV agent, by high-performance liquid chromatography in plasma from rat, dog and human. Journal of chromatography. B, Biomedical sciences and applications. 2000 Jun; 742(2):267-75. doi: 10.1016/s0378-4347(00)00170-5. [PMID: 10901131]
Z Q Xu, E R Kern, L Westbrook, L B Allen, R W Buckheit, C K Tseng, T Jenta, M T Flavin. Plant-derived and semi-synthetic calanolide compounds with in vitro activity against both human immunodeficiency virus type 1 and human cytomegalovirus. Antiviral chemistry & chemotherapy. 2000 Jan; 11(1):23-9. doi: 10.1177/095632020001100102. [PMID: 10693651]
L Hanna. Calanolide A: a natural non-nucleoside reverse transcriptase inhibitor. BETA : bulletin of experimental treatments for AIDS : a publication of the San Francisco AIDS Foundation. 1999 Apr; 12(2):8-9. doi: . [PMID: 11366704]
R A Newman, W Chen, T L Madden. Pharmaceutical properties of related calanolide compounds with activity against human immunodeficiency virus. Journal of pharmaceutical sciences. 1998 Sep; 87(9):1077-80. doi: 10.1021/js980122d. [PMID: 9724557]
". Natural compound shows anti-HIV activity. AIDS patient care and STDs. 1998 May; 12(5):410. doi: ". [PMID: 11361986]
T C McKee, R W Fuller, C D Covington, J H Cardellina, R J Gulakowski, B L Krepps, J B McMahon, M R Boyd. New pyranocoumarins isolated from Calophyllum lanigerum and Calophyllum teysmannii. Journal of natural products. 1996 Aug; 59(8):754-8. doi: 10.1021/np9603784. [PMID: 8792623]
T Pengsuparp, L Cai, H Constant, H H Fong, L Z Lin, A D Kinghorn, J M Pezzuto, G A Cordell, K Ingolfsdóttir, H Wagner. Mechanistic evaluation of new plant-derived compounds that inhibit HIV-1 reverse transcriptase. Journal of natural products. 1995 Jul; 58(7):1024-31. doi: 10.1021/np50121a006. [PMID: 7561895]