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Chemistry

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Also known as: Huperzine a, 120786-18-7, ( inverted exclamation marka)-huperzine a, Fordine, Huperizine a, (-)-huperzine a

Molecular Formula

C₁₅H₁₈N₂O

Molecular Weight

242.32 g/mol

InChI Key

ZRJBHWIHUMBLCN-QDEBKDIKSA-N

(13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0,]trideca-2,4,6,10-tetraen-5-ol is a natural product found in Streptomyces coelicoflavus and Huperzia with data available.

1 2D Structure

Fordine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one

2.1.2 InChI

InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+

2.1.3 InChI Key

ZRJBHWIHUMBLCN-QDEBKDIKSA-N

2.1.4 Canonical SMILES

CC=C1C2CC3=C(C1(CC(=C2)C)N)C=CC(=O)N3

2.1.5 Isomeric SMILES

C/C=C/1\C2CC3=C(C1(CC(=C2)C)N)C=CC(=O)N3

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Huperzine A

2. Huperzine A, (5alpha,9beta,11z)-(-)-isomer

3. Fordine

2.2.2 Depositor-Supplied Synonyms

1. Huperzine A

2. 120786-18-7

3. ( Inverted Exclamation Marka)-huperzine A

4. Fordine

5. Huperizine A

6. (-)-huperzine A

7. (+)-huperzine A

8. (-)-huperzine A (hupa)

9. Huperzinea

10. Ncgc00159362-02

11. 102518-79-6

12. (?)-huperazine A

13. Schembl679315

14. Chembl394259

15. Schembl1047469

16. Chebi:91724

17. Huperzine A [(-)-huperzine A]

18. Dtxsid801115670

19. Hms1362i05

20. Hms1792i05

21. Hms3403i05

22. 103735-86-0

23. Akos022661860

24. Akos026750633

25. Cs-1089

26. Ncgc00163246-02

27. Ncgc00163246-03

28. 5,9-methanocycloocta(b)pyridin-2(1h)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-

29. As-75811

30. Hy-17388

31. (+/-)-huperzine A, Synthetic, >=98% (tlc)

32. Brd-a47065382-001-02-9

33. (11e)-5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1h)-one

34. (13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5,10-tetraen-5-ol

35. (afae'a Centa' Nota Inverted Exclamation Markafasa'a Inverted Exclamation Markafae'adaggeratrade Markafa Centa Centa' Nota Inverted Exclamation Marka'a Not)-huperzine A

2.3 Create Date

2005-09-10

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₈N₂O
Molecular Weight	242.32 g/mol
XLogP3	0
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	242.141913202 g/mol
Monoisotopic Mass	242.141913202 g/mol
Topological Polar Surface Area	55.1 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	551
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Cholinesterase Inhibitors

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)

Neuroprotective Agents

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)

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