(3R,5R,6R)-trihydroxy-7E-megastigmen-9-one

(3R,5R,6R)-trihydroxy-7E-megastigmen-9-one
Compound Structure:
Synonyms: (3S,5R,6R,7E)-3,5,6-Trihydroxy-7-megastigmen-9-one;(+/-)-e-4-(1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl)-but-3-en-2-one; (3E)-4-(1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl)but-3-en-2-one;(E)-4-(1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl)but-3-en-2-one
Compound ID: NMPC-025
PubChem ID:

51136538
Molecular Formula: C13H22O4
Canonical SMILES: CC(=O)C=CC1(C(CC(CC1(C)O)O)(C)C)O
InChIKey: QASOACWKTAXFSE-AATRIKPKSA-N
About the compound:

It has hydroxyl groups at positions 3, 5, and 6, a ketone functional group at position 9, and a double bond in the E (trans) configuration at position 7. The specified stereochemistry is given by the (3S,5R,6R) configuration. Norisoprenoids, including various megastigmenes, are found in a wide variety of plants. Their formation is often related to the degradation of carotenoids.They are commonly found in fruits and flowers, and their presence often contributes to aroma and flavor. In fact, certain norisoprenoids are significant aroma compounds in some wines and fruits. Due to their aromatic properties, certain norisoprenoids, including megastigmenes, are valuable in the flavor and fragrance industry.
Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

666.8 g/mol

XLogP3-AA

2.7

Hydrogen Bond Donor Count

8

Hydrogen Bond Acceptor Count

11

Rotatable Bond Count

5

Exact Mass

666.39791266 g/mol

Monoisotopic Mass

666.39791266 g/mol

Topological Polar Surface Area

197Ų

Heavy Atom Count

47

Formal Charge

0

Complexity

1270

Isotope Atom Count

0

Defined Atom Stereocenter Count

16

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Source: PubChem
Source Species: Ficus thonningii
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