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1617-70-5 | LUPENONE
CAS No: 1617-70-5 Catalog No: AG001VTA MDL No:MFCD00083578
Product Description
Catalog Number:
AG001VTA
Chemical Name:
LUPENONE
CAS Number:
1617-70-5
Molecular Formula:
C30H48O
Molecular Weight:
424.7015
MDL Number:
MFCD00083578
IUPAC Name:
(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
InChI:
InChI=1S/C30H48O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-23,25H,1,9-18H2,2-8H3/t20-,21+,22-,23+,25+,27+,28-,29+,30+/m0/s1
InChI Key:
GRBHNQFQFHLCHO-BHMAJAPKSA-N
SMILES:
CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C
Properties
Complexity:
807
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
9
Defined Bond Stereocenter Count:
0
Exact Mass:
424.371g/mol
Formal Charge:
0
Heavy Atom Count:
31
Hydrogen Bond Acceptor Count:
1
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
424.713g/mol
Monoisotopic Mass:
424.371g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
17.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
9.6
Literature
| Title | Journal |
|---|---|
| Isolation, Structural Modification, and HIV Inhibition of Pentacyclic Lupane-Type Triterpenoids from Cassine xylocarpa and Maytenus cuzcoina. | Journal of natural products 20150522 |
| Chemical constituents of Anacolosa pervilleana and their antiviral activities. | Fitoterapia 20120901 |
| Flavonoids and other compounds from Ouratea ferruginea (Ochnaceae) as anticancer and chemopreventive agents. | Molecules (Basel, Switzerland) 20120703 |
| Synthesis and anti-HIV activity of lupane and olean-18-ene derivatives. Absolute configuration of 19,20-epoxylupanes by VCD. | Journal of natural products 20120427 |
| [Triterpene compounds from Cirsium setosum]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20120401 |
| Antiparasitic compounds from Cupania cinerea with activities against Plasmodium falciparum and Trypanosoma brucei rhodesiense. | Journal of natural products 20110425 |
| Phytotoxic, antifungal activities and acute toxicity studies of the crude extract and compounds from Diospyros canaliculata. | Natural product research 20110401 |
| [Chemical constituents from roots of Pueraria lobata]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20101201 |
| Chemical constituents of the bark of Dipteryx alata vogel, an active species against Bothrops jararacussu venom. | Molecules (Basel, Switzerland) 20101112 |
| [Studies on the triterpenoids constituents from Phyllodium elegans]. | Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20100501 |
| Structure-activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: potential impact in diabetes. | Journal of medicinal chemistry 20100114 |
| Inhibition of protein tyrosine phosphatase 1B by lupeol and lupenone isolated from Sorbus commixta. | Journal of enzyme inhibition and medicinal chemistry 20090801 |
| Novel 3alpha-methoxyserrat-14-en-21beta-ol (PJ-1) and 3beta-methoxyserrat-14-en-21beta-ol (PJ-2)-curcumin, kojic acid, quercetin, and baicalein conjugates as HIV agents. | Bioorganic & medicinal chemistry 20090715 |
| [Studies on chemical constituents of Liriope platyphylla]. | Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20070901 |
| Two triterpenes lupanone and lupeol isolated and identified from Tamarindus indica linn. | Pakistan journal of pharmaceutical sciences 20070401 |
| Preparative isolation and purification of chemical constituents from the root of Adenophora tetraphlla by high-speed counter-current chromatography with evaporative light scattering detection. | Journal of chromatography. A 20070119 |
| [Chemical constitutents of Bauhinia aurea]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20061201 |
| [Studies on chemical constituents of Balanophora spicata]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20061101 |
| [Studies on constituents in herb of Senecio scandens]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20061101 |
| [Compounds from marine mangrove plant Bruguiera sexangula var. rhynchopetala]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20060701 |
| Bioactive constituents of brazilian red propolis. | Evidence-based complementary and alternative medicine : eCAM 20060601 |
| Triterpenoids from Drypetes chevalieri Beille (euphorbiaceae). | Natural product research 20060520 |
| [Chemical investingation of Chinese mangrove Sonneratia apetala II]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20050801 |
| Lupane triterpenoids from Maytenus species. | Journal of natural products 20050701 |
| Antimicrobial activities of Barringtonia acutangula. | Phytotherapy research : PTR 20050601 |
| A new 3,4-seco-lupane derivative from Lasianthus gardneri. | Journal of natural products 20040501 |
| Constituents of the stem bark of Pongamia pinnata with the potential to induce quinone reductase. | Journal of natural products 20030901 |
| Constituents from the leaves of Phellodendron amurense var. wilsonii and their bioactivity. | Journal of natural products 20030901 |
| The Willgerodt-Kindler reaction on lupenone: unusual oxidative dimerization. | Natural product letters 20021001 |
| Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line. | Journal of natural products 20020501 |
| Antimycobacterial plant terpenoids. | Planta medica 20011101 |
| Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase. | Lipids 20010501 |
| Triterpenoids from Dysoxylum malabaricum. | Phytochemistry 20010201 |
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