Helminthosporol

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Description

Helminthosporol is a natural plant growth-regulator that can promote the growth of rice and lettuce seedlings. Helminthosporol can also inhibit the activity of acyl-CoA: cholesterol acyltransferase (ACAT) in rat liver microsomes and the synthesis of cholesterol esters in macrophages[1][2][3].

CAS Number

1619-29-0

UNSPSC

12352211

Target

Acyltransferase; Phytohormone

Related Pathways

Metabolic Enzyme/Protease; Others

Field of Research

Metabolic Disease

Smiles

OC[C@H]1[C@@]2([H])C(C=O)=C([C@@]1(CC[C@@H]2C(C)C)C)C

Molecular Formula

C15H24O2

Molecular Weight

236.35

References & Citations

[1]Li YY, et al. Bioactive seco-Sativene Sesquiterpenoids from an Artemisia desertorum Endophytic Fungus, Cochliobolus sativus. J Nat Prod. 2020 May 22;83 (5) :1488-1494.|[2]Tamura S, et al. Isolation of helminthosporol as a natural plant growth-regulator and its chemical structure. Agricultural and Biological Chemistry, 1965, 29 (3) : 216-221.|[3]PARK J K O O, et al. Inhibition of acyl-CoA: cholesterol acyltransferase by helminthosporol and its related compounds. The Journal of Antibiotics, 1993, 46 (8) : 1303-1305.

Shipping Conditions

Room temperature

Scientific Category

Natural Products

Clinical Information

No Development Reported

Chemical Information

Helminthosporol

(1R,4R,5S,8S)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carbaldehyde has been reported in Bipolaris, Drechslera, and Bipolaris sorokiniana with data available.

CAS Number	1619-29-0
PubChem CID	160583
IUPAC Name	(1R,4R,5S,8S)-8-(hydroxymethyl)-1,7-dimethyl-4-propan-2-ylbicyclo[3.2.1]oct-6-ene-6-carbaldehyde
Molecular Formula	C15H24O2
Molecular Weight	236.35
XLogP	2.6
Topological Polar Surface Area	37.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Heavy Atom Count	17
Formal Charge	0
Complexity	356

SMILES

CC1=C([C@H]2[C@H](CC[C@@]1([C@H]2CO)C)C(C)C)C=O

InChI

InChI=1S/C15H24O2/c1-9(2)11-5-6-15(4)10(3)12(7-16)14(11)13(15)8-17/h7,9,11,13-14,17H,5-6,8H2,1-4H3/t11-,13+,14-,15+/m1/s1

InChIKey

JNDNSKMAFGPBFU-BEAPCOKYSA-N

Chemical Structure

2D Structure

CAS: 1619-29-0

CID: 160583

Formula: C15H24O2

MW: 236.35

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	236.35
XLogP3	2.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Exact Mass	236.177630004
Monoisotopic Mass	236.177630004
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	356
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
TN8976-01	Helminthosporol

Helminthosporol

Chemical Information

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