Machaeriol A

CAS Number

• 377077-52-6

PubChem CID

• 10089121

ChemSpider

• 8264658

ChEMBL

• ChEMBL494422

Machaeriol A

Identifiers
IUPAC name (6aS,9S,10aS)-6,6,9-trimethyl-3-[(E)-2-phenylethenyl]-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
CAS Number	377077-52-6
PubChem CID	10089121
ChemSpider	8264658
ChEMBL	ChEMBL494422
Chemical and physical data
Formula	C24H28O2
Molar mass	348.486 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@H]1CC[C@H]2[C@H](C1)C3=C(C=C(C=C3OC2(C)C)/C=C/C4=CC=CC=C4)O
InChI InChI=1S/C24H28O2/c1-16-9-12-20-19(13-16)23-21(25)14-18(15-22(23)26-24(20,2)3)11-10-17-7-5-4-6-8-17/h4-8,10-11,14-16,19-20,25H,9,12-13H2,1-3H3/b11-10+/t16-,19-,20-/m0/s1 Key:KCNFZTIIENBEPU-TUCATBTLSA-N

Machaeriol A is one of a number of phytocannabinoids with a hexahydrocannabinol backbone, found in plants from the Machaerium family such as Machaerium multiflorum. While they are related in structure to tetrahydrocannabinols such as those from cannabis, the machaeriol compounds have opposite trans stereochemistry from THC and have no affinity for the psychoactive CB₁ receptor. However, some derivatives are active at CB₂ and if synthesized as their (-)-trans isomers they would retain CB1/CB2 activity, and they have also been found to have antibacterial, antifungal and antiparasitic actions, and have been investigated as lead compounds for the development of potential anti-cancer drugs.^{[1][2][3][4][5][6][7][8][9][10]}