Table S4 u The "effective" chemical compounds that significantly (> 3 s.d. or < - 3 s.d.) alter the period-length ofboth mouse and human clock cells.SName aStructure Name b

Function cAmsacrinehydrochloride

4-(9-Acridinylamino)-N(methanesulfonyl)-m-anisidinehydrochloride

DNA topoisomerase II inhibitor (35)

Ketoconazole

cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4yl]methoxy]phenyl]-piperazine

Potent inhibitor of cytochrome P450c17 enzyme; antifungal agent (36)
GABA-C receptor antagonist; powerful, nonspecific CNS stimulant isolated
from Anamirta cocculin (37)

Picrotoxin
SB 216763

3-(2,4-Dichlorophenyl)-4-(1-methyl-1H-indol3-yl)-1H-pyrrole-2,5-dione

Potent, selective, cell permeable inhibitor of glycogen synthetase kinase-3(GSK-3) (38)

BP 897N-[4-(4-(2-methoxyphenyl)piperazinyl)butyl]2-naphthamide

Partially selective D3 dopamine receptor agonist (39)9-Cp-Ade

9-cyclopentyladenine

Cell-permeable, non-competitive adenylyl cyclase inhibitor; targets the P-sitedomain (40)2-Chloroadenosine

6-Amino-2-chloropurine riboside

Adenosine receptor agonist with selectivity for A1 over A2 (41)

Cyproterone acetate

6-Chloro-1beta,2beta-dihydro-17-hydroxy3'H-cyclopropa(1,2)-pregna-1,4,6-triene3,20-dione acetate

Androgen antagonist; synthetic steroid (42)

Chloro-IB-MECA

2-Chloro-N6-(3-iodobenzyl)-adenosine-5'-Nmethyluronamide

A3 adenosine receptor agonist (43)

(R,R)-cis-Diethyl
tetrahydro-2,8chrysenediol(5R, 11R)-5,11-Diethyl-5,6,11,12-tetrahydro2,8-chrysenediol

Potent estrogen receptor beta antagonist; potent partial agonist at estrogen
receptor alpha (44)cis-(Z)-Flupenthixol
dihydrochloride
IB-MECAIIK7Phenamilmethanesulfonate
SB206553
hydrochloride(Z)-4-[3-[2-(Trifluoromethyl)-9H-thioxanthen9-ylidene]propyl]-1-piperazine-ethanol
dihydrochloride
1-Deoxy-1-[6-[[(3-iodophenyl)
methyl]amino]-9H-purin-9-yl]-N-methyl-betaD-ribofuranuronamide
N-Butanoyl 2-(9-methoxy-6H-isoindolo[2,1a]indol-11-yl)ethanamine
3,5-Diamino-6-chloro-N[imino(phenylamino)methyl]pyrazinecarboxamide methansulfonate
N-3-Pyridinyl3,5-dihydro-5-methyl-benzo[1,2-b:4,5b']dipyrrole-1(2H)-carboxamidehydrochloride

Dopamine receptor antagonist; antipsychotic (45)Selective A3 adenosine receptor agonist (43)Melatonin receptor agonist (46)
Irreversible inhibitor of amiloride-sensitive Na
amiloride (47)+channels; derivative ofPotent 5-HT2C/5-HT2B serotonin receptor antagonist (48)

Trequinsinhydrochloride

HL 725

Phosphodiesterase III (PDE III) inhibitor (49)

CGP 57380

N3-(4-fluorophenyl)-1h-pyrazolo[3,4d]pyrimidine-3,4-diamine

Cell-permeable, selective mitogen-activated protein kinase-interacting kinase
1 (MNK1) inhibitor (50)

(R)-(+)-WIN 55,212-2mesylate(R)-(+)-[2,3-Dihydro-5-methyl3[(morpholinyl)methyl]pyrrolo[1,2,3-de]-1,4benzoxazinyl]-(1-naphthalenyl)methanone mesylate

High affinity cannabinoid receptor agonist (51)

The alias (Name) (a), structure name (b), and shortly summarized functions of the compounds (c) are listed.
The upper four compounds colored gray are those that shortened the period, and the others that lengthened
the period. See also Table S3, in which "potent effective" compounds that markedly (> 10 s.d.) alter the periodlength of both clock cells are also listed.