ID: ALA501711

Max Phase: Preclinical

Molecular Formula: C35H52O4

Molecular Weight: 536.80

Molecule Type: Small molecule

Representations

Synonyms (1): Hyperforin
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)=CCC[C@]1(C)[C@@H](CC=C(C)C)C[C@@]2(CC=C(C)C)C(=O)[C@]1(C(=O)C(C)C)C(=O)C(CC=C(C)C)=C2O

Standard InChI:  InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1

Standard InChI Key:  KGSZHKRKHXOAMG-HQKKAZOISA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 536.80

Molecular Weight (Monoisotopic): 536.3866

AlogP: 8.99

#Rotatable Bonds: 11

Polar Surface Area: 71.44

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.67

CX Basic pKa:

CX LogP: 9.67

CX LogD: 7.00

Aromatic Rings: 0

Heavy Atoms: 39

QED Weighted: 0.21

Np Likeness Score: 2.64

References

1. Verotta L, Appendino G, Belloro E, Bianchi F, Sterner O, Lovati M, Bombardelli E..  (2002)  Synthesis and biological evaluation of hyperforin analogues. Part I. Modification of the enolized cyclohexanedione moiety.,  65  (4): [PMID:11975475] [10.1021/np0105681]

2. Verotta L, Appendino G, Jakupovic J, Bombardelli E..  (2000)  Hyperforin analogues from St. John's wort (Hypericum perforatum).,  63  (3): [PMID:10757735] [10.1021/np9903752]

3. Nahrstedt A, Butterweck V..  (2010)  Lessons learned from herbal medicinal products: the example of St. John's Wort (perpendicular).,  73  (5): [PMID:20408551] [10.1021/np1000329]

4. PubChem BioAssay data set, 

5.  (2008)  Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition, 

6.  (2008)  Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition, 

7. Kast HR, Goodwin B, Tarr PT, Jones SA, Anisfeld AM, Stoltz CM, Tontonoz P, Kliewer S, Willson TM, Edwards PA..  (2002)  Regulation of multidrug resistance-associated protein 2 (ABCC2) by the nuclear receptors pregnane X receptor, farnesoid X-activated receptor, and constitutive androstane receptor.,  277  (1): [PMID:11706036] [10.1074/jbc.m109326200]

8. Tirona RG, Leake BF, Wolkoff AW, Kim RB..  (2003)  Human organic anion transporting polypeptide-C (SLC21A6) is a major determinant of rifampin-mediated pregnane X receptor activation.,  304  (1): [PMID:12490595] [10.1124/jpet.102.043026]

9. Schmidt S, Jürgenliemk G, Schmidt TJ, Skaltsa H, Heilmann J..  (2012)  Bi-, tri-, and polycyclic acylphloroglucinols from Hypericum empetrifolium.,  75  (10): [PMID:23030826] [10.1021/np300237n]

10. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

11. Hanke T, Dehm F, Liening S, Popella SD, Maczewsky J, Pillong M, Kunze J, Weinigel C, Barz D, Kaiser A, Wurglics M, Lämmerhofer M, Schneider G, Sautebin L, Schubert-Zsilavecz M, Werz O..  (2013)  Aminothiazole-featured pirinixic acid derivatives as dual 5-lipoxygenase and microsomal prostaglandin E2 synthase-1 inhibitors with improved potency and efficiency in vivo.,  56  (22): [PMID:24171493] [10.1021/jm401557w]

12. Yang XW, Li MM, Liu X, Ferreira D, Ding Y, Zhang JJ, Liao Y, Qin HB, Xu G..  (2015)  Polycyclic Polyprenylated Acylphloroglucinol Congeners Possessing Diverse Structures from Hypericum henryi.,  78  (4): [PMID:25871261] [10.1021/acs.jnatprod.5b00057]

13. Crockett S,Baur R,Kunert O,Belaj F,Sigel E.  (2016)  A new chromanone derivative isolated from Hypericum lissophloeus (Hypericaceae) potentiates GABAA receptor currents in a subunit specific fashion.,  24  (4.0): [PMID:26791864] [10.1016/j.bmc.2015.12.037]

14. Chang YH, Hung HY..  (2022)  Recent advances in natural anti-obesity compounds and derivatives based on in vivo evidence: A mini-review.,  237  [PMID:35489224] [10.1016/j.ejmech.2022.114405]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• TP-search Transporter Database